| Date & Time | Game | Venue |
|---|---|---|
| Dec. 14, 6:40 PM | (0) Masconomet Chieftains at (7) St. John's Prep Eagles | Essex Sports Center |
| Dec. 17, 4:30 PM | (5) Masconomet Chieftains at (4) Marblehead Magicians | O'Keefe Athletic Center Salem State |
| Dec. 21, 8:05 PM | (1) Danvers Falcons at (4) Masconomet Chieftains | Haverhill Valley Forum |
| Dec. 27, 4:00 PM | (0) Masconomet Chieftains at (3) Stoneham Spartans
Stoneham Christmas Tournament |
Stoneham Arena |
| Dec. 30, 4:00 PM | (1) Masconomet Chieftains at (2) Dedham Marauders
Stoneham Christmas Classic - Consolation Game |
Stoneham Arena |
| Jan. 4, 7:30 PM | (7) Masconomet Chieftains at (4) Swampscott Big Blue | McVann-O'Keefe Skating Rink |
| Jan. 7, 5:20 PM | (4) Gloucester Fishermen at (2) Masconomet Chieftains | Haverhill Valley Forum |
| Jan. 9, 6:45 PM | (2) Newburyport Clippers at (7) Masconomet Chieftains | Haverhill Valley Forum |
| Jan. 14, 7:30 PM | (2) Beverly Panthers at (5) Masconomet Chieftains | Lawrence Valley Forum |
| Jan. 16, 6:00 PM | (1) Masconomet Chieftains at (2) Lincoln-Sudbury Warriors | New England Sports Center |
| Jan. 21, 3:30 PM | (3) Masconomet Chieftains at (4) Winthrop Vikings
OT |
Larsen Rink |
| Feb. 1, 5:05 PM | (4) Marblehead Magicians at (3) Masconomet Chieftains | Haverhill Valley Forum |
| Feb. 4, 6:00 PM | (2) Masconomet Chieftains at (5) Gloucester Fishermen | Dorothy Talbot Rink |
| Feb. 6, 7:30 PM | (3) Masconomet Chieftains at (0) Danvers Falcons | Essex Sports Center |
| Feb. 8, 7:45 PM | (3) Peabody/Saugus Tanners at (11) Masconomet Chieftains | Haverhill Valley Forum |
| Feb. 11, 6:00 PM | (5) Masconomet Chieftains at (2) Bishop Fenwick Crusaders | McVann-O'Keefe Skating Rink |
| Feb. 15, 8:05 PM | (2) Winthrop Vikings at (5) Masconomet Chieftains | Haverhill Valley Forum |
| Feb. 17, 7:10 PM | (0) Masconomet Chieftains at (3) Andover Golden Warriors | Breakaway Ice Center |
| Feb. 21, 5:00 PM | (1) Masconomet Chieftains at (3) Malden Catholic Lancers | Valley Forum II |
| Feb. 23, 1:00 PM | (1) North Andover Scarlet Knights at (6) Masconomet Chieftains | Essex Sports Center |
| Mar. 1, 8:05 PM | (4) Wilmington Wildcats at (0) Masconomet Chieftains
MIAA D2 Boys State Tournament - First Round |
Haverhill Valley Forum |
