| Date | Location | Result | |
| 3/1/00 | ROBERTS STADIUM (Evansville, IN) | MISSOURI-ST. LOUIS (#3 Seed) 62, SOUTHERN INDIANA (#6 Seed) 57 | Box score |
| 2/26/00 | PAC ARENA (Evansville, IN) | #4 NORTHERN KENTUCKY 61, SOUTHERN INDIANA 48 | Box score |
| 2/24/00 | PAC ARENA (Evansville, IN) | INDIANAPOLIS 74, SOUTHERN INDIANA 70 | Box score |
| 2/19/00 | KNIGHTS HALL (Louisville, KY) | BELLARMINE 76, SOUTHERN INDIANA 60 | Box score |
| 2/17/00 | Owensboro Sportscenter (Ky.) | SOUTHERN INDIANA 76, KENTUCKY WESLEYAN 68 | Box score |
| 2/15/00 | PAC ARENA (Evansville, IN) | SIU EDWARDSVILLE 72, SOUTHERN INDIANA 68 | Box score |
| 2/12/00 | NEIL CAREY ARENA (Romeoville, IL) | SOUTHERN INDIANA 86, LEWIS 80 | Box score |
| 2/10/00 | Kenosha, WI | SOUTHERN INDIANA 59, WISCONSIN-PARKSIDE 54 | Box score |
| 2/5/00 | PAC ARENA (Evansville, IN) | INDIANA/PURDUE FT. WAYNE 70, SOUTHERN INDIANA 68 | Box score |
| 2/3/00 | PAC ARENA (Evansville, IN) | SOUTHERN INDIANA 77, SAINT JOSEPH'S 57 | Box score |
| 1/29/00 | NICOSON HALL (INDIANAPOLIS, IN) | SOUTHERN INDIANA 85, INDIANAPOLIS 65 | Box score |
| 1/27/00 | NKU REGENTS HALL (Highland Heights, KY) | #8 NORTHERN KENTUCKY 80, SOUTHERN INDIANA 51 | Box score |
| 1/22/00 | PAC ARENA (Evansville, IN) | SOUTHERN INDIANA 86, KENTUCKY WESLEYAN 79 | Box score |
| 1/20/00 | PAC ARENA (Evansville, IN) | BELLARMINE 78, SOUTHERN INDIANA 73 | Box score |
| 1/15/00 | PAC ARENA (Evansville, IN) | SOUTHERN INDIANA 78, WISCONSIN-PARKSIDE 68 | Box score |
| 1/13/00 | PAC ARENA (Evansville, IN) | LEWIS 72, SOUTHERN INDIANA 53 | Box score |
| 1/8/00 | PAC ARENA (Evansville, IN) | SOUTHERN INDIANA 58, QUINCY 47 | Box score |
| 1/6/00 | MARK TWAIN BUILDING (St. Louis, MO) | MISSOURI-ST. LOUIS 82, SOUTHERN INDIANA 74 | Box score |
| 12/30/99 | PAC ARENA (Evansville, IN) | SOUTHERN INDIANA 76, KENTUCKY STATE 45 | Box score |
| 12/20/99 | PAC Arena (Evansville, IN) | SOUTHERN INDIANA 104, SPALDING 61 | Box score |
| 12/18/99 | Kirksville, MO (Pershing Arena) | SOUTHERN INDIANA 82, TRUMAN STATE 78 | Box score |
| 12/11/99 | Edwardsville, IL | SOUTHERN INDIANA 74, SIU EDWARDSVILLE 69 | Box score |
| 12/4/99 | Rensselaer, IN | SAINT JOSEPH'S 74, SOUTHERN INDIANA 72 | Box score |
| 12/2/99 | Ft. Wayne, IN | SOUTHERN INDIANA 78, INDIANA/PURDUE FT. WAYNE 63 | Box score |
| 11/29/99 | PAC ARENA (Evansville, IN) | SOUTHERN INDIANA 80, OAKLAND CITY 67 | Box score |
| 11/20/99 | St. Joseph, MO | NEBRASKA KEARNEY 62, SOUTHERN INDIANA 55 | Box score |
| 11/19/99 | St. Joseph, MO | SOUTHERN INDIANA 63, ROCKHURST 57 | Box score |