Stadium: Alumni Field Round: 1
| NCAAF | 2019/09/28 18:00 | Westfield State Owls v Massachusetts Maritime Buccaneers | L | 7-31 |
| NCAAF | 2018/10/06 16:00 | Massachusetts Maritime Buccaneers v Westfield State Owls | W | 24-38 |
| NCAAF | 2019/11/16 17:00 | Westfield State Owls v Umass Dartmouth Corsairs | L | 13-19 |
| NCAAF | 2019/11/09 17:00 | Westfield State Owls v Worcester State Lancers | W | 38-15 |
| NCAAF | 2019/10/26 18:00 | Fitchburg State Falcons v Westfield State Owls | W | 7-26 |
| NCAAF | 2019/10/19 20:00 | Western Connecticut Colonials v Westfield State Owls | L | 62-28 |
| NCAAF | 2019/10/12 16:00 | Westfield State Owls v Plymouth State Panthers | L | 13-38 |
| NCAAF | 2019/10/05 16:00 | Bridgewater State Bears v Westfield State Owls | L | 41-17 |
| NCAAF | 2019/09/28 18:00 | Westfield State Owls v Massachusetts Maritime Buccaneers | L | 7-31 |
| NCAAF | 2019/09/21 16:00 | Framingham State Rams v Westfield State Owls | L | 48-21 |
| NCAAF | 2019/11/16 17:00 | Massachusetts Maritime Buccaneers v Bridgewater State Bears | L | 21-26 |
| NCAAF | 2019/11/09 17:00 | Umass Dartmouth Corsairs v Massachusetts Maritime Buccaneers | W | 14-28 |
| NCAAF | 2019/11/02 16:00 | Massachusetts Maritime Buccaneers v Framingham State Rams | L | 6-16 |
| NCAAF | 2019/10/26 17:00 | Plymouth State Panthers v Massachusetts Maritime Buccaneers | L | 7-3 |
| NCAAF | 2019/10/19 16:00 | Massachusetts Maritime Buccaneers v Fitchburg State Falcons | W | 37-0 |
| NCAAF | 2019/10/12 21:00 | Western Connecticut Colonials v Massachusetts Maritime Buccaneers | L | 38-21 |
| NCAAF | 2019/10/05 16:00 | Massachusetts Maritime Buccaneers v Worcester State Lancers | W | 28-13 |
| NCAAF | 2019/09/28 18:00 | Westfield State Owls v Massachusetts Maritime Buccaneers | W | 7-31 |