| Date & Time | Game | Venue |
|---|---|---|
| Dec. 14, 6:00 PM | (1) Wellesley Raiders at (2) Milton Wildcats | Ulin Memorial Rink |
| Dec. 18, 8:00 PM | (6) Milton Wildcats at (4) Walpole Timberwolves | Cadillac Ice Arena |
| Dec. 21, 6:00 PM | (0) Weymouth Wildcats at (4) Milton Wildcats | Ulin Memorial Rink |
| Dec. 23, 3:00 PM | (1) Dedham Marauders at (5) Milton Wildcats | Ulin Memorial Rink |
| Dec. 27, 2:00 PM | (2) Milton Wildcats at (4) Duxbury Dragons
Tenney Cup |
The Bog |
| Dec. 29, 2:00 PM | (3) Milton Wildcats at (4) Bishop Feehan Shamrocks
Tenney Cup |
The Bog |
| Jan. 1, 12:00 PM | (7) Archbishop Williams Bishops at (1) Milton Wildcats
Tenney Cup |
The Bog |
| Jan. 4, 2:30 PM | (5) Milton Wildcats at (2) Braintree Wamps | Zapustas Arena |
| Jan. 8, 6:45 PM | (5) Milton Wildcats at (4) Needham Rockets
Milton wins in OT |
Babson Skating Center |
| Jan. 11, 7:20 PM | (3) Milton Wildcats at (2) Natick Red Hawks
Milton wins in OT |
Chase Arena |
| Jan. 15, 7:00 PM | (1) Newton North/South Tigers at (2) Milton Wildcats | Ulin Memorial Rink |
| Jan. 18, 5:30 PM | Milton Wildcats at Martha's Vineyard Vineyarders | Martha's Vineyard Arena |
| Jan. 19 (Time TBA) | TBD at Milton Wildcats
Martha's Vineyard Tournament |
Martha's Vineyard Arena |
| Jan. 22, 7:00 PM | Marshfield Rams at Milton Wildcats | Ulin Memorial Rink |
| Jan. 25, 6:00 PM | Framingham Flyers at Milton Wildcats | Ulin Memorial Rink |
| Jan. 29, 7:00 PM | Needham Rockets at Milton Wildcats | Ulin Memorial Rink |
| Feb. 1, 6:00 PM | Milton Wildcats at Brookline Warriors | Warrior Ice Arena |
| Feb. 5, 7:00 PM | Walpole Timberwolves at Milton Wildcats | Ulin Memorial Rink |
| Feb. 8 (Time TBA) | Milton Wildcats at Weymouth Wildcats | Connell Memorial Rink |
| Feb. 12, 7:00 PM | Braintree Wamps at Milton Wildcats | Ulin Memorial Rink |
| Feb. 19, 7:00 PM | Winchester Red & Black at Milton Wildcats | Ulin Memorial Rink |
