| 9/14/2019 | Williams (7-2,7-2) | 13 | at | Middlebury | 17 | |||
| 9/21/2019 | Middlebury | 28 | at | Bates (2-7,2-7) | 0 | |||
| 9/28/2019 | Trinity CT (5-4,5-4) | 27 | at | Middlebury | 32 | |||
| 10/5/2019 | Middlebury | 34 | at | Amherst (4-5,4-5) | 31 | 2OT | ||
| 10/12/2019 | Colby (2-7,2-7) | 26 | at | Middlebury | 27 | |||
| 10/19/2019 | Wesleyan (8-1,8-1) | 21 | at | Middlebury | 45 | |||
| 10/26/2019 | Middlebury | 47 | at | Bowdoin (0-9,0-9) | 29 | |||
| 11/2/2019 | Hamilton (4-5,4-5) | 7 | at | Middlebury | 14 | |||
| 11/9/2019 | Middlebury | 31 | at | Tufts (4-5,4-5) | 24 |
| vs Middlebury | vs Other Opponents | Middlebury compared to OOs | |
| Record: | 0-9 | 36-36 | |
| Points Scored: | 19.78 | 23.57 | 3.79 |
| Points Allowed: | 30.56 | 23.57 | 6.99 |
| Margin: | -10.78 | 0.00 | 10.78 |
| Total Points: | 50.34 | 47.14 | 3.20 |