| Date & Time | Game | Venue |
|---|---|---|
| December 11, 2025 | (2) North Attleboro Red Rocketeers at (5) Wellesley Raiders | Boston Sports Institute |
| December 13, 2025 | (0) Wellesley Raiders at (4) Milton Wildcats | Ulin Memorial Rink |
| December 17, 2025 | (2) Newton North Tigers at (4) Wellesley Raiders | Wellesley Sports Center |
| December 20, 2025 | (1) Wellesley Raiders at (0) Brookline Warriors
Wellesley wins in OT |
Walter Brown Arena |
| December 23, 2025 | (4) Needham Rockets at (3) Wellesley Raiders
Needham win in OT |
Wellesley Sports Center |
| December 27, 2025 | (1) Wellesley Raiders at (5) Falmouth Clippers
Ray Kenney Classic |
Falmouth Ice Arena |
| December 28, 2025 | (2) Plymouth South Panthers at (3) Wellesley Raiders
Ray Kenny Christmas Classic |
Falmouth Ice Arena |
| January 03, 2026 | (4) Framingham Flyers at (0) Wellesley Raiders | Wellesley Sports Center |
| January 07, 2026 | (2) Walpole Timberwolves at (3) Wellesley Raiders
Wellesley wins in OT |
Wellesley Sports Center |
| January 10, 2026 | (4) Wellesley Raiders at (5) Needham Rockets
Needham Wins in OT |
Babson Skating Center |
| January 14, 2026 | (5) Natick Red Hawks at (2) Wellesley Raiders | Wellesley Sports Center |
| January 19, 2026 | (1) North Middlesex Patriots at (4) Wellesley Raiders | Wellesley Sports Center |
| January 24, 2026 | (0) Wellesley Raiders at (1) Weymouth Wildcats | Connell Memorial Rink |
| January 28, 2026 | (1) Braintree Wamps at (0) Wellesley Raiders | Wellesley Sports Center |
| January 30, 2026 | (4) Wellesley Raiders at (2) Newton North Tigers | John A. Ryan Arena |
| February 01, 2026 | (3) Wellesley Raiders at (5) North Attleboro Red Rocketeers | New England Sports Village |
| February 04, 2026 | (2) Brookline Warriors at (3) Wellesley Raiders | Wellesley Sports Center |
| February 07, 2026 | (1) Wellesley Raiders at (3) Framingham Flyers | Loring Arena |
| February 11, 2026 | (0) Wellesley Raiders at (6) Natick Red Hawks | Chase Arena |
| February 16, 2026 | (1) Plymouth North Eagles at (5) Wellesley Raiders | Wellesley Sports Center |
| February 24, 2026 | (1) Medford Mustangs at (4) Wellesley Raiders
MIAA D1 - Boys State Tournament - Preliminary Round |
Boston Sports Institute |
| February 26, 2026 | (3) Wellesley Raiders at (4) Xaverian Hawks
MIAA D1 - Boys State Tournament - Round 32 |
Canton Ice House |
