| 9/16/2023 | Amherst (4-5,4-5) | 7 | at | Middlebury | 21 | |||
| 9/23/2023 | Middlebury | 21 | at | Wesleyan (6-3,6-3) | 24 | |||
| 9/30/2023 | Bowdoin (4-5,4-5) | 27 | at | Middlebury | 34 | |||
| 10/7/2023 | Middlebury | 12 | at | Williams (3-6,3-6) | 10 | |||
| 10/14/2023 | Middlebury | 20 | at | Trinity CT (8-1,8-1) | 15 | |||
| 10/21/2023 | Bates (0-9,0-9) | 7 | at | Middlebury | 48 | |||
| 11/4/2023 | Middlebury | 41 | at | Hamilton (3-6,3-6) | 7 | |||
| 11/11/2023 | Tufts (6-3,6-3) | 10 | at | Middlebury | 19 | |||
| 11/18/2023 | Middlebury | 35 | at | Colby (3-6,3-6) | 28 | Postponed from 10/28/23 |
| vs Middlebury | vs Other Opponents | Middlebury compared to OOs | |
| Record: | 1-8 | 36-36 | |
| Points Scored: | 15.00 | 23.44 | 8.44 |
| Points Allowed: | 27.89 | 23.44 | 4.45 |
| Margin: | -12.89 | 0.00 | 12.89 |
| Total Points: | 42.89 | 46.88 | -3.99 |