2019 First Round at John Carroll
Centre 1, Kalamazoo 0

2001 First Round at Chicago
Kalamazoo 1, Wheaton 0
2001 Second Round
Ohio Wesleyan 3, Kalamazoo 2 (OT)

2000 First Round at Wilmington
Wilmington 5, Kalamazoo 0 

1990 First Round
Ohio Wesleyan 1, Kalamazoo 0

1988 First Round at Ohio Wesleyan
Kalamazoo 2, Ohio Wesleyan 2 (Kalamazoo advanced by Penalty Kicks)
1988 Second Round
Wheaton 0, Kalamazoo 0 (Wheaton advanced by Penalty Kicks)

1986 First Round
Ohio Wesleyan 2, Kalamazoo 1

1985 First Round
Wheaton 0, Kalamazoo 0 (Wheaton advanced by Penalty Kicks)