| Day | Date | Opponent | Location | TV | Outcome/Time |
| Thu | 11/04/1999 | NBC Thunder (exhibition) | Champaign, Ill.
(Assembly Hall) | | W, 104-87
Recap | Stats |
| Mon | 11/15/1999 | Cimeba All-Stars (exhibition) | Champaign, Ill.
(Assembly Hall) | | W, 82-69
Recap | Stats |
| Fri | 11/19/1999 | Western Illinois | Champaign, Ill.
(Assembly Hall) | ESPN+ | W, 76-53
Recap | Stats | Quotes | Notes | Archived Audio |
| Mon | 11/22/1999 | Bradley | Peoria, Ill. | WCIA/WEEK-TV | W, 72-62
Recap | Stats | Archived Audio |
| Tue | 11/30/1999 | Duke | Chicago | ESPN | L, 72-69
Recap | Stats | Archived Audio |
| Sat | 12/04/1999 | Maryland | Washington, D.C.
(BB&T Classic) | WICD/Fox Sports-Chicago | L, 69-67
Recap | Stats | Archived Audio |
| Sun | 12/05/1999 | Seton Hall (3rd Place Game) | Washington, D.C.
(BB&T Classic) | WICD/Fox Sports-Chicago | W, 72-61
Recap | Stats | Archived Audio |
| Wed | 12/08/1999 | Texas-Pan American | Champaign, Ill.
(Assembly Hall) | | W, 98-61
Recap | Stats | Archived Audio |
| Sat | 12/11/1999 | Kansas State | Champaign, Ill.
(Assembly Hall) | ESPN+ | W, 81-48
Recap | Stats | Archived Audio |
| Sat | 12/18/1999 | Kansas | Chicago | ESPN | W, 84-70
Recap | Stats | Archived Audio |
| Tue | 12/21/1999 | Missouri | St. Louis | ESPN+ | L, 78-72
Recap | Stats | Archived Audio |
| Tue | 12/28/1999 | Bethune-Cookman | Champaign, Ill.
(Assembly Hall) | | W, 97-47
Recap | Stats | Archived Audio |
| Thu | 12/30/1999 | Loyola | Champaign, Ill.
(Assembly Hall) | ESPN+ | W, 107-71
Recap | Stats | Archived Audio |
| Thu | 01/06/2000 | Ohio State | Champaign, Ill.
(Assembly Hall) | ESPN2 | W, 80-77
Recap | Stats | Archived Audio | Archived Live Stats |
| Sat | 01/08/2000 | Wisconsin | Madison, Wis. | ESPN+R | L, 63-59
Recap | Stats | Archived Audio |
| Wed | 01/12/2000 | Purdue | Champaign, Ill.
(Assembly Hall) | ESPN+ | L, 69-66
Recap | Stats | Archived Audio |
| Sun | 01/16/2000 | Michigan | Ann Arbor, Mich. | CBS | L, 95-91 (OT)
Recap | Stats | Archived Audio |
| Sat | 01/22/2000 | Penn State | Champaign, Ill.
(Assembly Hall) | ESPN+ | W, 87-76
Recap | Stats | Archived Audio | Archived Live Stats |
| Wed | 01/26/2000 | Iowa | Iowa City, Iowa | ESPN+ | W, 69-58
Recap | Stats | Archived Audio |
| Sun | 01/30/2000 | Michigan State | East Lansing, Mich. | CBS | L, 91-66
Recap | Stats | Archived Audio |
| Wed | 02/02/2000 | Minnesota | Champaign, Ill.
(Assembly Hall) | ESPN+ | W, 73-59
Recap | Stats | Archived Audio | Archived Live Stats |
| Sun | 02/06/2000 | Penn State | University Park, Pa. | ESPN+R | W, 51-50
Recap | Stats | Archived Audio |
| Wed | 02/09/2000 | Michigan | Champaign, Ill.
(Assembly Hall) | ESPN+ | W, 75-59
Recap | Stats | Archived Audio | Archived Live Stats |
| Sat | 02/12/2000 | Iowa | Champaign, Ill.
(Assembly Hall) | ESPN+R | W, 78-50
Recap | Stats | Archived Audio | Archived Live Stats |
| Thu | 02/17/2000 | Minnesota | Minneapolis | ESPN | W, 89-80
Recap | Stats | Archived Audio |
| Sat | 02/19/2000 | Northwestern | Evanston, Ill. | ESPN+ | W, 63-30
Recap | Stats | Archived Audio |
| Tue | 02/22/2000 | Indiana | Champaign, Ill.
(Assembly Hall) | ESPN | W, 87-63
Recap | Stats | Archived Live Stats |
| Sun | 02/27/2000 | Ohio State | Columbus, Ohio | CBS | L, 64-51
Recap | Stats | Archived Audio |
| Sat | 03/04/2000 | Northwestern | Champaign, Ill.
(Assembly Hall) | ESPN+R or ESPN+ | W, 73-44
Recap | Stats | Archived Audio | Archived Live Stats |
| Fri | 03/10/2000 | Indiana | Chicago
(Big Ten Tournament) | ESPN 2 | W, 72-69
Recap | Stats | Quotes | Archived Audio |
| Sat | 03/11/2000 | Penn State | Chicago
(Big Ten Semifinals) | CBS | W, 94-84
Recap | Stats |
| Sun | 03/12/2000 | Michigan State | Chicago
(Big Ten Finals) | CBS | L, 76-61
Recap | Stats | Archived Audio |
| Fri | 03/17/2000 | Pennsylvania | Winston-Salem, N.C.
(NCAA 1st Round) | CBS | W, 68-58
Recap | Stats | Archived Audio |
| Sun | 03/19/2000 | Flordia | Winston-Salem, N.C.
(NCAA 2nd Round) | CBS | L, 93-76
Recap | Stats | Archived Audio |
