| Date & Time | Game | Venue |
|---|---|---|
| Dec. 14, 5:30 PM | (1) Milton Wildcats at (1) Wellesley Raiders | Boston Sports Institute |
| Dec. 14, 5:30 PM | (1) Milton Wildcats at (1) Wellesley Raiders | Wellesley Sports Center |
| Dec. 18, 7:00 PM | (2) Walpole Timberwolves at (6) Milton Wildcats | Ulin Memorial Rink |
| Dec. 21, 7:30 PM | (2) Milton Wildcats at (2) Weymouth Wildcats | Connell Memorial Rink |
| Dec. 23, 2:00 PM | (2) Milton Wildcats at (2) Canton Bulldogs | Canton Metropolis Rink |
| Dec. 26, 4:00 PM | (3) Barnstable Red Hawks at (1) Milton Wildcats
North Quincy-Holiday Tournament |
Quincy Youth Arena |
| Dec. 28, 2:00 PM | (3) Nantucket Whalers at (8) Milton Wildcats
North Quincy-Holiday Tournament |
Quincy Youth Arena |
| Jan. 1, 2:00 PM | (2) Nauset Warriors at (2) Milton Wildcats
Tie Game |
Ulin Memorial Rink |
| Jan. 4, 6:00 PM | (1) Braintree Wamps at (1) Milton Wildcats | Ulin Memorial Rink |
| Jan. 8, 7:00 PM | (5) Needham Rockets at (2) Milton Wildcats | Ulin Memorial Rink |
| Jan. 11, 6:00 PM | (2) Natick Red Hawks at (0) Milton Wildcats | Ulin Memorial Rink |
| Jan. 15, 4:00 PM | (6) Milton Wildcats at (2) Newton North Tigers | John A. Ryan Arena |
| Jan. 18, 6:00 PM | (3) St. Mary's Lynn Spartans at (0) Milton Wildcats | Ulin Memorial Rink |
| Jan. 22, 5:30 PM | (1) Milton Wildcats at (1) Plymouth North Eagles | Armstrong Arena |
| Jan. 25, 4:50 PM | (4) Milton Wildcats at (4) Framingham Flyers | Loring Arena |
| Jan. 29, 6:50 PM | (1) Milton Wildcats at (0) Needham Rockets | Babson Skating Center |
| Feb. 1, 6:00 PM | (0) Brookline Warriors at (3) Milton Wildcats | Ulin Memorial Rink |
| Feb. 5, 8:00 PM | (1) Milton Wildcats at (0) Walpole Timberwolves
Milton wins in OT |
Cadillac Ice Arena |
| Feb. 8, 6:00 PM | (1) Weymouth Wildcats at (2) Milton Wildcats | Ulin Memorial Rink |
| Feb. 12, 6:00 PM | (0) Milton Wildcats at (4) Braintree Wamps | Zapustas Arena |
| Feb. 18, 2:00 PM | (4) Milton Wildcats at (3) Westford Academy Ghosts
(OT) Irish American Shoot Out Tournament |
O'Brien Arena |
| Feb. 20, 2:00 PM | (0) Milton Wildcats at (3) Woburn Tanners
Irish American Shoot Out Tournament - Championship Game |
O'Brien Arena |
| Feb. 25, 7:00 PM | (2) Plymouth North Eagles at (4) Milton Wildcats
MIAA D2 BOYS STATE TOURNAMENT - Round 32 |
Ulin Memorial Rink |
| Mar. 1, 6:00 PM | (2) Newburyport Clippers at (3) Milton Wildcats
MiAA D2 BOYS STATE TOURNAMENT - Round 16 |
Ulin Memorial Rink |
| Mar. 5, 7:15 PM | (2) Milton Wildcats at (5) Canton Bulldogs
MIAA D2 BOYS STATE TOURNAMENT - Round 8 |
Gallo Arena |
