Stadium: Alumni Field Round: 1
| NCAA Division I, FCS, Playoffs | 2018/10/06 16:00 | Massachusetts Maritime Buccaneers v Westfield State Owls | W | 24-38 |
| NCAA Division I, FCS, Playoffs | 2019/09/21 16:00 | Framingham v Westfield State Owls | L | 48-21 |
| NCAA Division I, FCS, Playoffs | 2019/09/13 23:00 | Westfield State Owls v Western New England Golden Bears | L | 35-56 |
| NCAA Division I, FCS, Playoffs | 2019/09/07 17:00 | Union Dutchmen v Westfield State Owls | L | 42-7 |
| NCAA Division I, FCS, Playoffs | 2018/11/10 17:00 | Western Connecticut Colonials v Westfield State Owls | W | 13-27 |
| NCAA Division I, FCS, Playoffs | 2018/10/27 17:00 | Westfield State Owls v Plymouth State Panthers | L | 7-10 |
| NCAA Division I, FCS, Playoffs | 2018/10/20 18:00 | Westfield State Owls v Framingham | L | 2-27 |
| NCAA Division I, FCS, Playoffs | 2018/10/12 23:00 | Fitchburg v Westfield State Owls | W | 27-41 |
| NCAA Division I, FCS, Playoffs | 2018/10/06 16:00 | Massachusetts Maritime Buccaneers v Westfield State Owls | W | 24-38 |
| NCAA Division I, FCS, Playoffs | 2019/09/21 16:00 | Maine Maritime Mariners v Massachusetts Maritime Buccaneers | W | 21-42 |
| NCAA Division I, FCS, Playoffs | 2019/09/13 23:00 | Massachusetts Maritime Buccaneers v Suny Maritime Privateers | W | 31-14 |
| NCAA Division I, FCS, Playoffs | 2018/11/10 17:00 | Bridgewater v Massachusetts Maritime Buccaneers | L | 21-7 |
| NCAA Division I, FCS, Playoffs | 2018/11/03 16:00 | Umass Dartmouth Corsairs v Massachusetts Maritime Buccaneers | L | 20-0 |
| NCAA Division I, FCS, Playoffs | 2018/10/27 16:00 | Massachusetts Maritime Buccaneers v Worcester State Lancers | W | 26-0 |
| NCAA Division I, FCS, Playoffs | 2018/10/20 17:00 | Plymouth State Panthers v Massachusetts Maritime Buccaneers | L | 17-14 |
| NCAA Division I, FCS, Playoffs | 2018/10/13 17:00 | Massachusetts Maritime Buccaneers v Western Connecticut Colonials | L | 13-23 |
| NCAA Division I, FCS, Playoffs | 2018/10/06 16:00 | Massachusetts Maritime Buccaneers v Westfield State Owls | L | 24-38 |