| Date | Location | Result | |
| 2/22/00 | Williamstown, Mass. | Williams 74, Middlebury 54 | Box score |
| 2/19/00 | Middlebury, Vt. | Tufts 86, Middlebury 84 | Box score |
| 2/18/00 | Middlebury, Vt. | Middlebury 80, Bates 65 | Box score |
| 2/12/00 | Waterville, Maine | Middlebury 64, Colby 57 | Box score |
| 2/11/00 | Brunswick, Maine | Bowdoin 47, Middlebury 45 | Box score |
| 2/8/00 | Middlebury, Vt. | Middlebury 90, Norwich 69 | Box score |
| 2/5/00 | Middlebury, Vt. | Amherst 69, Middlebury 66 | Box score |
| 2/4/00 | Middlebury, Vt. | Trinity 74, Middlebury 57 | Box score |
| 1/29/00 | Middletown, Conn. | Wesleyan 65, Middlebury 57 | Box score |
| 1/28/00 | New London, Conn. | Connecticut College 74, Middlebury 53 | Box score |
| 1/22/00 | Middlebury, Vt. | Middlebury 69, Union 63 | Box score |
| 1/15/00 | Middlebury, Vt. | Hamilton 83, Middlebury 77 | Box score |
| 1/14/00 | Middlebury, Vt. | Middlebury 88, Johnson St. 64 | Box score |
| 1/11/00 | Waltham, Mass. | Brandeis 79, Middlebury 73 | Box score |
| 1/8/00 | Middlebury, Vt. | Springfield 81, Middlebury 67 | Box score |
| 12/9/99 | Middlebury, Vt. | Middlebury 84, Castleton St. 60 | Box score |
| 12/7/99 | N. Adams, Mass. | Middlebury 62, Massachusetts College 60 | Box score |
| 12/5/99 | Northfield, Vt. | Middlebury 81, Castleton St. 61 | Box score |
| 12/4/99 | Northfield, Vt. | Colby-Sawyer 73, Middlebury 69 | Box score |
| 11/30/99 | Saratoga, N.Y. | Skidmore 71, Middlebury 63 | Box score |
| 11/23/99 | Middlebury, Vt. | Middlebury 72, Washington & Lee 69 | Box score |
| 11/20/99 | Plattsburgh, N.Y. | York 69, Middlebury 54 | Box score |
| 11/19/99 | Plattsburgh, N.Y. | Middlebury 67, Plattsburgh St. 63 | Box score |