1997 Pioneer Bowl I @ Herndon Stadium
Kentucky State University - 30
Livingstone College - 26

1998 Pioneer Bowl II @ Herndon Stadium
Tuskegee University - 23
Livingstone College - 9

1999 Pioneer Bowl III @ GA Dome
Winston Salem State University - 23
Tuskegee University - 7

2000 Pioneer Bowl IV @ GA Dome
Tuskegee University - 12
Winston Salem State University - 9

2001 Pioneer Bowl V @ GA Dome
Tuskegee University - 28
Virginia Union University - 0

2003 Pioneer Bowl VI @ GA Dome
Albany State University - 52
Fayetteville State University - 30

2004 Pioneer Bowl VII @ Ladd-Peebles Stadium
Shaw University - 30
Tuskegee University - 28

2005 Pioneer Bowl VIII @ American Legion Memorial Stadium
Tuskegee University - 28
Bowie State University - 26

2006 Pioneer Bowl IX @ American Legion Memorial Stadium
Tuskegee University - 17
Johnson C. Smith University - 7

2007 Pioneer Bowl X @ Charlie W. Johnson Football Stadium
Tuskegee University - 58
Virginia Union University - 51