Past winners of the Bob O'Connor Bowl played for between Cubs and Lions

Cubs hold the most wins with a 15 to 4 majority

1985 - Cubs
1986 - Cubs
1987 - Cubs
1988 - Cubs
1989 - Cubs
1990 - Cubs
1991 - Cubs
1992 - Lions
1993 - Cubs
1994 - Lions
1995 - Cubs
1996 - Lions
1997 - Cubs
1998 - Lions
1999 - Cubs
2000 - Cubs
2001 - Cubs
2018 - Cubs
2019 - Cubs