| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (4) Masconomet Chieftains at (1) Gloucester Fishermen
Blaf "9" Memorial Game |
Dorothy Talbot Rink |
| December 18, 2019 | (1) Algonquin Titans at (1) Gloucester Fishermen | Dorothy Talbot Rink |
| December 21, 2019 | (5) Triton Vikings at (1) Gloucester Fishermen | Dorothy Talbot Rink |
| December 27, 2019 | (2) Westfield Bombers at (2) Gloucester Fishermen | Dorothy Talbot Rink |
| December 28, 2019 | (3) Marblehead Magicians at (2) Gloucester Fishermen
Cape Ann Savings Bank Tournament |
Dorothy Talbot Rink |
| January 04, 2020 | (3) Gloucester Fishermen at (1) Winthrop Vikings | Larsen Rink |
| January 06, 2020 | (6) Gloucester Fishermen at (4) Wayland Warriors | New England Sports Center |
| January 08, 2020 | (1) Swampscott Big Blue at (5) Gloucester Fishermen | Dorothy Talbot Rink |
| January 11, 2020 | (2) Gloucester Fishermen at (4) Marblehead Magicians | Rockett Arena |
| January 15, 2020 | (2) Danvers Falcons at (3) Gloucester Fishermen
Rivalry Game |
Dorothy Talbot Rink |
| January 18, 2020 | (4) Gloucester Fishermen at (1) Saugus Sachems | Kasabuski Arena |
| January 22, 2020 | (3) Gloucester Fishermen at (1) Beverly Panthers | Raymond J. Bourque Arena |
| January 29, 2020 | (0) Winthrop Vikings at (4) Gloucester Fishermen | Dorothy Talbot Rink |
| February 01, 2020 | (1) Peabody/Salem Tanners at (6) Gloucester Fishermen | Dorothy Talbot Rink |
| February 05, 2020 | (5) Marblehead Magicians at (2) Gloucester Fishermen | Dorothy Talbot Rink |
| February 08, 2020 | (3) Gloucester Fishermen at (3) Danvers Falcons | Raymond J. Bourque Arena |
| February 12, 2020 | (9) Gloucester Fishermen at (1) Lynn Jets | Connery Memorial Arena |
| February 15, 2020 | (1) Beverly Panthers at (7) Gloucester Fishermen | Dorothy Talbot Rink |
| February 19, 2020 | (3) Lynnfield Pioneers at (4) Gloucester Fishermen | Dorothy Talbot Rink |
| February 25, 2020 | (1) Wakefield Warriors at (5) Gloucester Fishermen
Boys D2 N Playoff |
Stoneham Arena |
| February 28, 2020 | (5) Gloucester Fishermen at (6) Lincoln-Sudbury Warriors
Boys D2 N Playoff |
O'Brien Arena |
