| Date & Time | Game | Venue |
|---|---|---|
| December 14, 2019 | (3) Ashland Clockers at (6) Norwood Mustangs | Rodman Arena |
| December 21, 2019 | (3) Ashland Clockers at (3) Medfield Warriors | Pirelli Veterans Arena |
| December 23, 2019 | (4) Ashland Clockers at (4) St. Peter Marian Guardians | Hart Center |
| December 26, 2019 | (8) Ashland Clockers at (0) East Boston Jets
East Boston DEEP FREEZE TOURNAMENT |
Lt. Porrazzo Memorial Rink |
| December 27, 2019 | (1) Ashland Clockers at (7) Dedham Marauders
Deep Freeze Cancer Tournament |
Lt. Porrazzo Memorial Rink |
| December 30, 2019 | (2) Nantucket Whalers at (3) Ashland Clockers | Gallo Arena |
| January 04, 2020 | (1) Dover-Sherborn/Weston Raiders at (7) Ashland Clockers | Loring Arena |
| January 06, 2020 | (6) Hopkinton Hillers at (1) Ashland Clockers | New England Sports Center |
| January 08, 2020 | (3) Holliston Panthers at (2) Ashland Clockers | Loring Arena |
| January 11, 2020 | (5) Dedham Marauders at (2) Ashland Clockers | Loring Arena |
| January 14, 2020 | (3) Ashland Clockers at (6) Westwood Wolverines | Canton Ice House |
| January 18, 2020 | (4) Ashland Clockers at (4) Medway Mustangs | Pirelli Veterans Arena |
| January 20, 2020 | (4) St. Peter Marian Guardians at (10) Ashland Clockers | Loring Arena |
| January 22, 2020 | (2) Ashland Clockers at (7) Hopkinton Hillers | New England Sports Center |
| January 25, 2020 | (6) Norwood Mustangs at (3) Ashland Clockers | Loring Arena |
| January 29, 2020 | (0) Norton Lancers at (6) Ashland Clockers | Loring Arena |
| February 01, 2020 | (2) Medfield Warriors at (2) Ashland Clockers | Loring Arena |
| February 05, 2020 | (5) Ashland Clockers at (2) Bellingham Blackhawks | Pirelli Veterans Arena |
| February 08, 2020 | (0) Ashland Clockers at (4) Holliston Panthers | Loring Arena |
| February 12, 2020 | (7) Westwood Wolverines at (4) Ashland Clockers | Loring Arena |
