| Year | Date | Opponent | Us | Them | Result | W | L | T | OT | Where | Location | Field | Coach | Notes | |
| 1909 | 11/25 | Toronto | 5 | 11 | L | 1 | Away | Toronto | |||||||
| 1921 | 9/23 | Toronto | 0 | 6 | L | 1 | Home | Bridgeport | Shop 14 Grounds | Walter Randolph | |||||
| 1927 | 9/24 | Toronto | 0 | 0 | T | 1 | Home | Bridgeport | Perkins Field | Julius McElroy | |||||
| 1928 | 9/28 | Toronto | 6 | 0 | W | 1 | Away | Toronto | Kaul Field | John Castilow | |||||
| 1931 | 10/16 | Toronto | 0 | 0 | T | 1 | Away | Toronto | Toronto Stadium | Floyd Baker | |||||
| 1932 | 10/15 | Toronto | 14 | 0 | W | 1 | Away | Toronto | Toronto Stadium | Floyd Baker | |||||
| 1933 | 10/13 | Toronto | 6 | 0 | W | 1 | Away | Toronto | Toronto Stadium | Jay Nevada | |||||
| 1934 | 10/12 | Toronto | 0 | 0 | T | 1 | Away | Toronto | Toronto Stadium | Jay Nevada | |||||
| 1936 | 10/31 | Toronto | 0 | 21 | L | 1 | Away | Toronto | Toronto Stadium | Orville Edmundson | |||||
| 1940 | 11/2 | Toronto | 13 | 13 | T | 1 | Away | Toronto | Toronto Stadium | Stanley Plummer | |||||
| 1941 | 11/1 | Toronto | 7 | 6 | W | 1 | Home | Bridgeport | Perkins Field | Ken Douds | |||||
| 1951 | 11/9 | Toronto | 6 | 7 | L | 1 | Away | Toronto | Toronto Stadium | George Kovalick | |||||
| 1952 | 11/7 | Toronto | 7 | 19 | L | 1 | Home | Bridgeport | Perkins Field | Al Blatnick | |||||
| 1996 | 9/21 | Toronto | 54 | 0 | W | 1 | Home | Bridgeport | Perkins Field | Rick Goodrich | |||||
| 1997 | 9/19 | Toronto | 9 | 13 | L | 1 | Away | Toronto | Clarke Hinkle Field | Rick Goodrich | |||||
| 1998 | 9/26 | Toronto | 0 | 46 | L | 1 | Home | Bridgeport | Perkins Field | Rick Goodrich | |||||
| 1999 | 9/17 | Toronto | 26 | 60 | L | 1 | Away | Toronto | Clarke Hinkle Field | Jim Fogle | |||||
| 2000 | 9/16 | Toronto | 12 | 41 | L | 1 | Home | Bridgeport | Perkins Field | Jim Fogle | |||||
| 2001 | 9/14 | Toronto | 22 | 40 | L | 1 | Away | Toronto | Clarke Hinkle Field | Ron Busby | |||||
| 2002 | 9/14 | Toronto | 14 | 45 | L | 1 | Home | Bridgeport | Perkins Field | Ron Busby | |||||
| 2003 | 9/12 | Toronto | 6 | 34 | L | 1 | Away | Toronto | Clarke Hinkle Field | Rudy Vavrock | |||||
| 2005 | 9/16 | Toronto | 13 | 20 | L | 1 | Away | Toronto | Clarke Hinkle Field | Rudy Vavrock | |||||
| 2010 | 9/3 | Toronto | 42 | 0 | W | 1 | Home | Bridgeport | Perkins Field | Rudy Vavrock | |||||
| 2011 | 9/2 | Toronto | 14 | 22 | L | 1 | Away | Toronto | Clarke Hinkle Field | Rudy Vavrock | |||||
| 2012 | 8/31 | Toronto | 20 | 19 | W | 1 | Home | Bridgeport | Perkins Field | Rudy Vavrock | |||||
| 2013 | 9/6 | Toronto | 14 | 35 | L | 1 | Away | Toronto | Clarke Hinkle Field | Rudy Vavrock | |||||
| 2014 | 9/5 | Toronto | 8 | 36 | L | 1 | Home | Bridgeport | Perkins Field | Rudy Vavrock | |||||
| 2015 | 9/4 | Toronto | 0 | 37 | L | 1 | Away | Toronto | Clarke Hinkle Field | Zach Melton | |||||
| 2016 | 9/2 | Toronto | 8 | 54 | L | 1 | Home | Bridgeport | Perkins Field | Zach Melton | |||||
| 2017 | 9/1 | Toronto | 22 | 60 | L | 1 | Away | Toronto | Clarke Hinkle Field | Gary Krol | |||||
| 2018 | 8/31 | Toronto | 0 | 36 | L | 1 | Home | St. Clairsville | Red Devil Stadium | Fred Ray | |||||
| 348 | 681 | 7 | 20 | 4 | .290 | ||||||||||
| 11.23 | 21.97 | -10.74 |