Chicago Cubs: My favorite memory vs. every National League team

Here I present my favorite Chicago Cubs memory against every National League team. Some were easy to pick; others, not so much.

The Chicago Cubs have been in the National League for a long, long time. They have a long-standing rivalry with some of the teams and have played many memorable games against those opponents. With other National League clubs, they don’t have quite as strong of a rivalry and, therefore, not as many big moments.

However, with talk about possibly realigning the MLB teams this season (and maybe even beyond), it prompted me to think about my favorite Cubs memory against every NL team. Some of the decisions were easy, especially with organizations that they’ve met in the postseason, including the Atlanta Braves, San Francisco Giants, Los Angeles Dodgers, and St. Louis Cardinals. Other decisions were not so easy.

Still, researching this article brought back some beautiful memories from over the years and also prompted me to think about what a great league the National League has been for a long time. Whatever MLB does, NL rivalries still mean a lot to me.

Keep in mind that this is my list. I’ve been a Cubs fan since 1994, so I only included moments that have taken place since then. Your list might look completely different, depending on how long you’ve been a fan of the team. I wish I had indeed been around for some of the earlier Cubs’ seasons, so my list could be more comprehensive. But I think the fact that it’s personal is what makes it so unique.

With that, we’ll start with the NL West, then move to the NL East, and finally, we’ll cover the Cubs’ fellow NL Central teams. I hope this article brings back some great memories for you as it has for me.

Chicago Cubs: Arizona Diamondbacks

The Cubs and Diamondbacks had met once in the postseason, in 2007, when Arizona had little trouble putting away the Cubs in a three-game sweep of the NLDS. Beyond that, there aren’t many games that stand out as memorable between the two teams. Here are a few candidates for most memorable Cubs moment:

• May 12, 1998: Mark Grace became the first player ever to hit a home run into the swimming pool of what is now Chase Field. (It was the Diamondbacks’ inaugural season.) Grace also took a bases-loaded walk in the top of the ninth, the difference in a 7-6 Cubs win.
• July 27, 1998: During his memorable 1998 home run chase, Sammy Sosa hit two home runs, including his first career grand slam, and accounted for all six runs scored as the Cubs beat the Diamondbacks in Arizona, 6-2. Sosa’s second career grand slam would come the very next day in a Cubs loss.
• August 1, 2003: The newly-acquired Aramis Ramirez hit a walk-off single in the 14th inning as the Cubs beat the Diamondbacks at Wrigley Field, 4-3. Both teams had scored two runs in the 11th.
• May 9-11, 2008: The Cubs swept all three games from the Diamondbacks at Wrigley Field. The middle game of the series took place during my college commencement ceremony.
• September 4-6, 2015: The Cubs swept all three games from the Diamondbacks at Wrigley Field (again). The middle game was another brilliant Jake Arrieta performance.
• July 26, 2018: Down 6-4 in the bottom of the ninth, David Bote hit a two-run homer at Wrigley Field, followed by a walk-off homer from Anthony Rizzo.

This is a difficult decision, but I’m going to go with the 2018 game. I almost picked 2003, but in the end, back-to-back home runs to end a game are tough to beat.

Chicago Cubs: San Diego Padres

This one was also tough. There haven’t been a whole lot of Cubs-Padres memories that stand out to me over the years. Of course, older fans will remember one terrible memory, in 1984, when the Padres rallied to win three straight games and take the series over the Cubs in the NLCS.

Anyway, I looked through the archives, and here’s a list of some critical Cubs-Padres games over the years:

• April 1, 1996: Opening Day at Wrigley Field. The Padres had scored runs in both the eighth and ninth innings to tie the game and send it into extras. In the tenth, the Cubs loaded the bases off future Hall of Famer Trevor Hoffman. Mark Grace singled into left field to score Rey Sanchez, and the Cubs won 5-4.
• September 17, 1998: As the Cubs were trying to secure a playoff spot, they were facing the Padres in San Diego when the game went into extras. The recently acquired Gary Gaetti homered, again off Hoffman, to lead off the tenth, and Rod Beck made it hold up as the Cubs won, 4-3.
• June 2, 1999: After the Padres scored three in the ninth to take an 8-5 lead at Wrigley Field, the Cubs rallied for four off Hoffman in the bottom of the ninth to win, capped off by a three-run home run from Sammy Sosa.
• August 5-7, 2003: With the Cubs in the middle of the NL Central division race, they went into San Diego and swept all three games. Mark Prior, Kerry Wood, and Carlos Zambrano earned wins.
• April 17-18, 2015: On the 17th, Kris Bryant made his major league debut, going 0-for-4 as the Padres won at Wrigley Field, 5-4. The next day, the Cubs blew a four-run ninth-inning lead but won it in the 11th on a Starlin Castro RBI single.

I’m going to go with Opening Day in 1996. I’ve always been an enormous Grace fan, and since it was Opening Day, that made it extra memorable.

Chicago Cubs: San Francisco Giants

There are two obvious candidates for the best moment between these two old National League foes, so I’ll just focus on those. The first one is the 1998 NL Wild Card tiebreaker game at Wrigley Field. 1998 was a magical year on the north side of Chicago, but a lot of people forget that the Giants had to make up five games on the Cubs with just ten games to go to force the tiebreaker game, held at Wrigley Field since the Cubs won a coinflip.

Steve Trachsel had an awful September, yet he came through for them with a strong performance in this game while a late Giants rally fell just short as the Cubs won, 5-3. They were quickly swept in the NLDS against the Atlanta Braves, yet I might not be a Cubs fan if it weren’t for this game. I was 13 years old, and my interest in the team was fading after the miserable 1997 season.

As great as that game was, the best Cubs-Giants moment has to come from the 2016 NLDS. Game 1 was an incredible back-and-forth pitching duel between Jon Lester and Johnny Cueto, and the Cubs eventually came out on top thanks to a Javier Baez eighth-inning home run. The Cubs won Game 2, but the Giants won Game 3 and lead Game 4 in San Francisco 5-2 after eight, leading some to believe the Giants could bring back that “even year” magic.

Then there was the most incredible, seemingly most improbable four-run ninth-inning rally that shocked even the most optimistic of Cubs faithful. Aroldis Chapman sealed the deal in the bottom of the ninth as the Cubs advanced to the NLCS for the second straight year. More people will remember the NLCS and the World Series, which were great in their own right, but that rally was one of those magical moments that we simply cannot forget.

Chicago Cubs: Los Angeles Dodgers

The Dodgers are responsible for one of my worst memories as a Cubs fan in 2008. They were the far inferior team against the Cubs in the NLDS, yet they made quick work of the Cubs in a three-game sweep.

But enough of that, you probably want to read about how the Cubs won the pennant against the Dodgers in 2016. Of course, there were several great moments in that series. Game 1 started with a bang, as the Cubs jumped out to a quick 3-0 before the Dodgers managed to tie the game in the top of the eighth. Miguel Montero then hit a grand slam in the bottom of the eighth to put the game away; some fans have said that’s the loudest they’ve ever heard Wrigley Field.

The Cubs were shut out in back-to-back Games 2 and 3, sending fans into a panic. However, a Ben Zobrist bunt in the top of the fourth sparked a rally, and the Cubs were on their way to relatively easy victories in Games 4 and 5.

I had tickets to a University of Michigan football game on the day of Game 6; for the first few innings, I had listened to Game 6 on the radio on the way home. I arrived at my parents’ house in time to catch most of the game on TV. As we know, the Cubs built a 5-0 lead and never wavered. Unlike Game 6 in 2003, there was little opportunity for drama, as Kyle Hendricks and Aroldis Chapman teamed up to shut out the Dodgers and clinch the pennant.

Though the World Series was still to follow, it felt like a huge weight had been lifted off of all our shoulders. For me, we finally got past the hurdle I’d been waiting 13 years for another opportunity to knockdown. There’s no question that this is my favorite National League moment in Cubs history.

Chicago Cubs: Miami Marlins

Here, I faced a big dilemma. The then-Florida Marlins are responsible for my worst Cubs memory in 2003. However, before Games 5, 6, and 7 happened, the Cubs took a three games to one lead. Game 3 was an intense 11 inning affair that ended when Luis Castillo got caught in a rundown between second and third base. Aramis Ramirez hit a grand slam in the first inning of Game 4 to help get the Cubs to within one game of the pennant.

I was ecstatic after that Game 4 victory. Do I consider that to be my favorite Cubs-Marlins moment? Or is it overshadowed by what happened afterward?

I looked back to try to find some memorable regular-season moments between these two teams, and they’re just aren’t many. Here are the best examples I could remember:

• July 27, 2008: Mike Fontenot hit a bases-clearing double off Joe Nelson that broke a 6-6 tie in the seventh inning as the Cubs beat the Marlins, 9-6. At the time, the Milwaukee Brewers were bearing down on the Cubs in the NL Central race, so this was a critical victory.
• August 15, 2008: Daryle Ward hit a three-run homer off Kevin Gregg in the top of the ninth in Miami as the Cubs beat the Marlins, 6-5.
• July 4, 2015: Kris Bryant homered twice in the first two innings, including a second-inning grand slam, as the Cubs beat the Marlins, 7-2.
• August 3, 2016: The Cubs rallied for three in the bottom of the ninth to beat the Marlins at Wrigley Field, 5-4.
• May 9, 2018: I was in attendance at Wrigley Field as the Cubs pounded the Marlins, 13-4.

Out of those games, the memory that means the most to me personally is the 2018 game I attended. However, in terms of the best game, I’ll go with the Bryant game from 2015. I suppose there are enough moments not to have to choose one from 2003.

Chicago Cubs: Philadelphia Phillies

Amazingly, the Phillies have never met in the postseason. They did play some wild games years ago before I was around.

I’ve attended two Phillies games at Wrigley Field that mean a lot to me. My first ever trip to Wrigley Field was on September 14, 1996. The Cubs lost to the Phillies, 6-2. I did get to see Ryne Sandberg hit a home run against his old team. Ozzie Timmons also homered for the Cubs.

The other Cubs-Phillies game I’ve attended was on May 4, 2017. It was my first trip back to Wrigley Field since the Cubs won the World Series. Down 4-3 in the bottom of the ninth, Miguel Montero homered to tie the game. It was a cold day, and the game went into 13 innings before the Cubs scored the winning run on a throwing error.

When we think about recent memorable games between these two teams, a lot of fans will recall June 6, 2018, when Jason Heyward hit a walk-off grand slam at Wrigley Field to beat the Phillies, 7-5. There’s also May 27-29, 2016, when the Cubs swept the Phillies at Wrigley Field to move to 34-14 on the season. Future manager David Ross, in his final playing season, hit his 100th career home run on the 27th.

Looking through all the years that the Cubs have been good in particular, there just aren’t many other memorable games that come to mind. The Heyward game was great, and I know a lot of fans remember that one fondly. However, I’m going to get personal with this one and go with the 2017 game I attended. It was a close, exciting game, unlike the Marlins game I attended, so that’s why I’ll give it the edge here.

Chicago Cubs: New York Mets

My first ever game that I watched as a Chicago Cubs fan was against the Mets, Opening Day 1994 at Wrigley Field. Tuffy Rhodes hit three home runs against Dwight Gooden, and though the Cubs lost the game, Rhodes had his 15 minutes of fame in the major leagues.

The Mets are part of two bad memories for me as a Cubs fan, and I wasn’t even around for 1969. In 2004, the Cubs blew a late 3-0 lead to the Mets in New York as part of their late-season collapse, and then there was the 2015 NLCS, a Mets sweep in which the Cubs’ bats failed to show up.

I looked through the archives to see if anything could compare to watching that first game in 1994. Here are a few notable games I found:

• May 3, 1996: Down 2-1 in the bottom of the ninth at Wrigley Field, Sammy Sosa came up with two on and hit a three-run homer off Paul Wilson as the Cubs earned a 4-2 win.
• March 31, 2003: On Opening Day in New York, Corey Patterson had four hits, two home runs, and seven RBIs as the Cubs pounded Tom Glavin and the Mets, 15-2.
• 2015: Before the Mets swept the Cubs in the playoffs, the Cubs swept the regular-season series from the Mets, winning all seven games.
• September 12-14, 2017: The Cubs swept all three games from the Mets, scoring a total of 39 runs.

I’m going to go with the Tuffy Rhodes game since it’s such an important game in my fandom. However, I’ve always been a big Patterson fan, so I guess I couldn’t go wrong with that choice, either.

Chicago Cubs: Washington Nationals

Before 2005, the Washington Nationals played in Montreal and were the Expos. I had to think hard, and I had a hard time coming up with many Cubs-Expos moments. There were a couple:

• April 3, 1998: The Cubs beat the Expos in the Cubs’ home opener, 6-2. The seventh-inning stretch tribute to Harry Caray still gets me to this day.
• April 8, 2003: The Cubs beast the Expos, 6-1, in the Cubs’ home opener.

As for after the team moved to our nation’s capital, two events immediately come to mind. One is from August 12, 2018, when the Cubs were playing the Nationals at Wrigley Field on ESPN’s Sunday Night Baseball. Max Scherzer had shut down the Cubs for most of the game, but they loaded the bases against Ryan Madson in the bottom of the ninth, down 3-0.

David Bote, who already had hit the crucial homer against the Diamondbacks mentioned above just a couple weeks prior, pinch-hit and ran the count to 2-2 before blasting a ball to center for a walk-off grand slam. Now that’s the ultimate dream we all have as kids: hitting a grand slam down by three runs with two outs in the bottom of the ninth.

However, I don’t think there’s much that can top Game 5 of the 2017 NLDS in Washington, a 9-8 Cubs victory. Aside from Game 7 of the 2016 World Series, considering what was on the line, that was the most intense Cubs game I ever watched, a dramatic back-and-forth contest that ended when Wade Davis struck out Bryce Harper on a low-and-in curveball. The Cubs would lose in the NLCS to the Dodgers, but I still have great memories of watching that game.

Chicago Cubs: Atlanta Braves

This one is pretty easy to decide, though there are a few noteworthy Cubs-Braves moments I also felt like mentioning:

• June 1-2, 2007: Though the Cubs lost these two games, the first game is famous for Carlos Zambrano-Michael Barrett fight in the dugout, while the second game is remembered for the Lou Piniella meltdown that is credited for helping to turn the season around.
• 2008: The Cubs swept the season series from the Braves. On June 12, at Wrigley Field, Jim Edmonds hit a game-tying homer in the ninth, while the Cubs won in the 11th when Reed Johnson was hit by a pitch with the bases loaded.
• August 20-23, 2015: The Cubs swept all four games from the Braves at Wrigley Field, including coming back from a 7-3 deficit on the 22nd.
• April 29, 2016: I was in attendance at Wrigley Field when Matt Szczur hit a grand slam late that put the game away.

However, the best Cubs-Braves moment has to be the 2003 NLDS victory. Kerry Wood pitched two great games, in Games 1 and 5, while Mark Prior threw a masterpiece in Game 3. This was a rematch of the 1998 NLDS, and both times, the Cubs were heavy underdogs. Unlike in 1998, however, the Cubs’ starting pitching made the difference.

Aside from everything that happened in 2016, this remains my next-favorite Cubs moment. It was the first time I had witnessed the Cubs win in the postseason (it was for many of us). Despite the rough ending to the season, I still feel a lot of joy when I think about that Game 5 victory against the Braves from 2003.

Chicago Cubs: Cincinnati Reds

I wish we had some Cubs-Reds division races to talk about, but in the time I’ve been following the team, there haven’t been any seasons in which both sides were really good. Therefore, coming up with a good Reds memory requires a little thinking. Here are some that came to mind:

• May 24, 2001: Jon Lieber, during his 20-win season, threw a one-hitter, facing the minimum 27 batters in a 3-0 Cubs win at Wrigley Field.
• April 4, 2003: Sammy Sosa hit his 500th career home run at Great American Ballpark off Scott Sullivan. The Cubs eventually lost the game.
• September 24, 2003: In a critical game down the stretch, Shawn Estes came through with a complete-game, four-hit shutout as the Cubs beat the Reds in Cincinnati, 8-0.
• April 16, 2004: Sammy Sosa and Moises Alou hit back-to-back home runs as the Cubs won, 11-10 at Wrigley Field.
• June 13-14, 2015: The Cubs earn back-to-back walk-off wins against the Reds at Wrigley Field, both on hits by Starlin Castro.
• April 21, 2016: Jake Arrieta threw a no-hitter as the Cubs beat the Reds, 16-0, in Cincinnati.
• June 27, 2016: Kris Bryant went 5-for-5 with three home runs and two doubles in an 11-8 Cubs win in Cincinnati. That was the first time in history that a batter accomplished that feat.

As we can see, it’s a lot more about individual performances than critical team wins. I’ll go with the Arrieta no-hitter since we don’t get to see no-hitters that often and Arrieta was in the middle of a dominant stretch. But don’t sleep on Lieber’s 2001 performance. In some ways, I think that performance was at least as impressive.

Chicago Cubs: Pittsburgh Pirates

There’s only been one season since I’ve been following in which both the Cubs and Pirates were really good, and that was in 2015. Two great memories stand out from that season. One of them took place on May 15, 2015, the game in which Gregory Polanco slipped and fell trying to catch a Matt Szczur pop-up, allowing the winning run to score in a wild 11-10, 12 inning victory at Wrigley Field.

Then there was the NL Wild Card game in Pittsburgh. The club had won 97 games during the regular season; the Pirates had won 98. The Cubs got to Gerrit Cole early, including a massive home run from Kyle Schwarber, while Jake Arrieta pitched a complete game shutout as the Cubs won, 4-0.

It was the first postseason victory in 12 years. Back in 2003, though the season ended poorly, I never imagined I’d have to wait that long to see that. However, that’s what made that victory so sweet.

As great as that game was, there’s another Cubs-Pirates memory that I’m going to pick for my favorite, and that is the doubleheader sweep from 2003 that allowed the Cubs to clinch the NL Central. I had to work during Game 1 and kept up with the score of that game, as well as the Houston Astros’ game, during my breaks.

The Astros’ loss meant that a Game 2 victory would clinch the division. And the Cubs put the game away early en route to a 7-2 win. It was my first time witnessing the Cubs clinch a division title. Of all the great memories I have of the 2003 season, that has to be one of my favorites. I’ll never forget how happy I was that day.

Chicago Cubs: Milwaukee Brewers

Cubs-Brewers has given us a lot of great contests over the years, while the teams have been involved in a few NL Central races together as well.

One of those races took place in 2007 when the squad eventually came out on top. A crucial game from that season was on June 29, when the Brewers jumped out to a quick 5-0 lead in the first inning at Wrigley Field. The team got to within 5-3 heading into the ninth when the Cubs rallied for three to win, capped by a two-run home run from Aramis Ramirez off Francisco Cordero. The Cubs were still looking up at the Brewers in the standings at the time, though it would prove to be a critical win late in the season.

Then there was 2008. Heading into a four-game series at Miller Park July 28-31, the Cubs were up on the Brewers by just one game. The Cubs put the Brewers in their place, sweeping all four games. And let’s not forget September 18, when the Cubs erased a 6-2 deficit in the ninth inning at Wrigley Field, capped by a three-run homer from Geovany Soto. The Cubs would eventually win in 12.

All that said, I’m going to let my personal bias take over here and say that my favorite memory took place on September 16, 2016, when I was in attendance at Wrigley Field. The Cubs had mathematically clinched the division the previous night when the Cardinals lost but hadn’t got to have a celebration yet.

Down 4-2 in the ninth, the Cubs rallied for two to tie it. Then, Miguel Montero homered to left to lead off the tenth for a walk-off win. Afterward, the Cubs celebrated their division title on the field. Though we all had much bigger goals in mind, it was a great afternoon to be at Wrigley.

Chicago Cubs: St. Louis Cardinals

The Cubs-Cardinals rivalry has given us many great moments over the years, for both sides. The Cardinals have the most recent good memory, sweeping the Cubs in a four-game series at Wrigley Field late in 2019, all games by one run. However, the Cubs have been on the positive side quite a few times as well.

Both in 2008 and 2017, the club clinched the NL Central division against the Cardinals; in 2008, it was at Wrigley Field, while it was in St. Louis in 2017. Those are great memories, indeed, but there are two that have to be considered among the best.

The first one took place on September 1-4, 2003, a five-game series at Wrigley Field (including a doubleheader on the 2nd). The two teams, along with the Houston Astros, were in a tight race for the NL Central division, and the Cubs were able to win four of the five games to gain the upper hand on St. Louis.

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The series is remembered for Dusty Baker and Tony LaRussa getting into a shouting match from their respective dugouts, yet four of the five games were intense. In the second game, the Cubs won in the 15th on a home run from Sammy Sosa, while they won the fourth and fifth game both by one run.

For years, that was my favorite Cubs-Cardinals memory. And then, the two teams met in the 2015 NLDS. For years, the fans had to watch as the Cardinals celebrated many times. And they got shut out in Game 1 of the series.

However, bad Cardinals defense in the second inning of Game 2 paved the way for a Chicago Cubs victory, and as we know, the team slugged their way to victory in Games 3 and 4 at Wrigley Field to win the series.

There was already plenty of joy in returning to the NLCS for the first time in 12 years. To do it against the much more successful division rival Cardinals made it that much sweeter. Though the team didn’t win the World Series that year, it felt like a huge hurdle had been overcome in the team’s history. For that reason, it’s hard to imagine any Cubs-Cardinals moment ever topping that.

Chicago Cubs: Houston Astros

Yes, I know the Houston Astros are now in the American League. However, they were in the National League for a long time until 2012. Therefore, I decided to add them as a bonus.

These two teams were involved in the dramatic NL Central race in 2003, yet there aren’t many head-to-head games that stand out from that season. Probably the most memorable was on May 31, when the two teams played 15 scoreless innings at Wrigley Field before Sammy Sosa singled in the winning run in the bottom of the 16th. Their final head-to-head meeting was August 19-21, when the Astros won two of three.

I’m also quite fond of September 2, 2007, when the team erased a 5-1 deficit late to beat the Astros at Wrigley Field, capped by a Derrek Lee homer in the eighth. We also had Carlos Zambrano’s no-hitter against the Astros in Milwaukee late in the 2008 season.

Then there was 1998 when Sammy Sosa hit his 66th and final home run off Jose Lima. However, I think most would agree that there’s a different 1998 moment that is the best from Cubs-Astros.

On May 6, 1998, Kerry Wood completed what many consider to be the most dominant pitching performance of all-time at Wrigley Field, against a potent Astros lineup. He allowed one hit, walked none, and struck out a record-tying 20 batters in what was just his fifth major league start. Amazingly, he had only gone more than five innings in one of his other previous starts.

It was an incredible performance, one that Chicago Cubs fans still get excited about when talking about today. In a season full of great memories, that has to be considered among the best, and certainly the best Cubs-Astros moment.