| Date & Time | Game | Venue |
|---|---|---|
| Dec. 9, 3:00 PM | (1) Shawsheen Rams at (2) Winthrop Vikings | Larsen Rink |
| Dec. 13, 6:10 PM | (3) Triton Vikings at (5) Winthrop Vikings | Larsen Rink |
| Dec. 16, 3:00 PM | (1) Danvers Falcons at (7) Winthrop Vikings | Larsen Rink |
| Dec. 26, 12:00 PM | (5) Winthrop Vikings at (2) Boston Latin Wolfpack
Michael Giordano Christmas Classic |
Murphy Memorial Rink |
| Dec. 27, 4:00 PM | (2) Hanover Hawks at (4) Winthrop Vikings
Michael Giordano Christmas Classic - Championship |
Murphy Memorial Rink |
| Jan. 6, 5:30 PM | (3) Winthrop Vikings at (1) Marblehead Magicians | Rockett Arena |
| Jan. 10, 6:10 PM | (3) Gloucester Fishermen at (5) Winthrop Vikings | Larsen Rink |
| Jan. 13, 6:00 PM | (7) Winthrop Vikings at (3) Swampscott Big Blue | Rockett Arena |
| Jan. 15, 7:00 PM | (2) Winthrop Vikings at (2) Lexington Minutemen
OT game ends in a tie |
Walter Brown Arena |
| Jan. 20, 8:00 PM | (4) Winthrop Vikings at (3) Masconomet Chieftains
Winthrop wins in OT |
Haverhill Valley Forum |
| Jan. 22, 5:30 PM | (2) Essex Tech Hawks at (5) Winthrop Vikings | Larsen Rink |
| Jan. 27, 1:00 PM | (1) Beverly Panthers at (5) Winthrop Vikings | Larsen Rink |
| Jan. 31, 8:30 PM | (5) Winthrop Vikings at (1) Danvers Falcons | Raymond J. Bourque Arena |
| Feb. 3, 1:00 PM | (4) Marblehead Magicians at (1) Winthrop Vikings | Larsen Rink |
| Feb. 7, 6:30 PM | (0) Winthrop Vikings at (2) Essex Tech Hawks | Essex Sports Center |
| Feb. 10, 6:00 PM | (1) Winthrop Vikings at (1) Gloucester Fishermen | Dorothy Talbot Rink |
| Feb. 12, 5:30 PM | (3) Medford Mustangs at (2) Winthrop Vikings
Medford wins in OT |
Larsen Rink |
| Feb. 14, 4:00 PM | (1) Masconomet Chieftains at (5) Winthrop Vikings | Larsen Rink |
| Feb. 17, 3:00 PM | (2) Peabody/Saugus Tanners at (13) Winthrop Vikings | Larsen Rink |
| Feb. 20, 2:30 PM | (3) Winthrop Vikings at (1) Grafton Gators | Buffone Arena |
| Feb. 28, 6:00 PM | (2) Tri-County Cougars at (9) Winthrop Vikings
MIAA D4 BOYS STATE TOURNAMENT - Round 32 |
Larsen Rink |
| Mar. 2, 2:00 PM | (1) Hudson Hawks at (6) Winthrop Vikings
MIAA D4 BOYS STATE TOURNAMENT - Sweet 16 |
Larsen Rink |
| Mar. 6, 7:30 PM | (0) Ashland Clockers at (7) Winthrop Vikings
MIAA D4 BOYS STATE TOURNAMENT - Elite 8 |
Stoneham Arena |
| Mar. 9, 3:00 PM | (2) Dover-Sherborn/Weston Raiders at (1) Winthrop Vikings
MIAA D4 BOYS STATE TOURNAMENT - Final 4 (2OT shootout) |
Gallo Arena |
