| 9/7/2019 | Redlands | 35 | at | George Fox (5-5) | 19 | at NWC | ||
| 9/14/2019 | Puget Sound (6-4) | 7 | at | Redlands | 58 | NWC | ||
| 9/21/2019 | Linfield (8-2) | 19 | at | Redlands | 27 | NWC | ||
| 10/5/2019 | Pomona-Pitzer (6-4,4-3) | 17 | at | Redlands | 38 | |||
| 10/12/2019 | Redlands | 18 | at | Chapman (10-1,7-0) | 21 | |||
| 10/19/2019 | Redlands | 45 | at | Claremont-Mudd-Scripps (5-5,3-4) | 6 | |||
| 10/26/2019 | La Verne (4-6,3-4) | 7 | at | Redlands | 65 | |||
| 11/2/2019 | Redlands | 33 | at | Cal Lutheran (5-5,4-3) | 14 | |||
| 11/9/2019 | Whittier (3-7,1-6) | 10 | at | Redlands | 45 | |||
| 11/16/2019 | Redlands | 67 | at | Occidental (0-8,0-7) | 12 | |||
| 11/23/2019 | Redlands | 14 | at | Mary Hardin-Baylor (12-1) | 43 | D3 Playoff round 1 | at ASWC |
| vs Redlands | vs Other Opponents | Redlands compared to OOs | |
| Record: | 2-9 | 62-39 | |
| Points Scored: | 15.91 | 33.89 | 17.98 |
| Points Allowed: | 40.45 | 24.54 | 15.91 |
| Margin: | -24.54 | 9.35 | 33.89 |
| Total Points: | 56.36 | 58.43 | -2.07 |