Chicago Cubs: Weeghman Region
- 1 seed Cap Anson vs. 16 seed Harry Steinfeldt
- 8 seed Greg Maddux vs. 9 seed George Gore
- 5 seed Hippo Vaughn vs. 12 seed King Kelly
- 4 seed Clark Griffith vs. 13 seed Charlie Hollocher
- 6 seed Charlie Root vs. 11 seed Johnny Kling
- 3 seed Frank Chance vs. 14 seed Larry French
- 7 seed Phil Cavarretta vs. 10 seed Larry Corcoran
- 2 seed Gabby Hartnett vs. 15 seed Kyle Hendricks
The Weeghman Region is host to the number 1 overall seed in the Cubs March Madness, Cap Anson. While Anson might not be a household name because he played in the 19th century, he is still one of the greatest offensive players in club history. His 3,012 hits and 1,880 RBI are both still tops in team history, with no real threats to either in sight.
Current Cub pitcher Hendricks is in this bracket, but as a 15 seed and a tough road out of the first round. One matchup that bears watching for sure is one of the greatest Cub pitchers of all time, but a guy who only spent half his career with the Cubs in Maddux. While he should have no problem with Gore in the first round, it’ll be an exciting matchup with top seed Anson in the round of 32.