| Date & Time | Game | Venue |
|---|---|---|
| December 15, 2021 | (6) Masconomet Chieftains at (1) Danvers Falcons | Essex Sports Center |
| December 18, 2021 | (2) Marblehead Magicians at (6) Masconomet Chieftains | Haverhill Valley Forum |
| Dec. 22 Postponed | Masconomet Chieftains at Newburyport Clippers
make-up TBA |
Graf Rink |
| December 28, 2021 | (1) Billerica Indians at (3) Masconomet Chieftains
Spartan Holiday Tournament |
Stoneham Arena |
| December 30, 2021 | (4) Masconomet Chieftains at (5) Stoneham Spartans
Stoneham Christmas Tournament |
Stoneham Arena |
| January 03, 2022 | (1) Bishop Fenwick Crusaders at (4) Masconomet Chieftains | Haverhill Valley Forum |
| January 05, 2022 | (1) Swampscott Big Blue at (5) Masconomet Chieftains | Essex Sports Center |
| January 08, 2022 | (4) Masconomet Chieftains at (3) Gloucester Fishermen | Dorothy Talbot Rink |
| January 10, 2022 | (5) Masconomet Chieftains at (2) Newburyport Clippers | Graf Rink |
| January 15, 2022 | (3) Masconomet Chieftains at (2) Beverly Panthers | Raymond J. Bourque Arena |
| January 17, 2022 | (3) Lincoln-Sudbury Warriors at (2) Masconomet Chieftains | Haverhill Valley Forum |
| January 22, 2022 | (1) Winthrop Vikings at (3) Masconomet Chieftains | Essex Sports Center |
| January 26, 2022 | (0) Danvers Falcons at (4) Masconomet Chieftains | Haverhill Valley Forum |
| Jan. 29 Postponed | Saugus Sachems at Masconomet Chieftains
PPD 1-29-22 Make-Up TBA |
Haverhill Valley Forum |
| February 02, 2022 | (5) Masconomet Chieftains at (4) Marblehead Magicians | Rockett Arena |
| February 05, 2022 | (4) Gloucester Fishermen at (5) Masconomet Chieftains | Essex Sports Center |
| February 07, 2022 | (5) Masconomet Chieftains at (2) Triton Vikings | Graf Rink |
| February 09, 2022 | (2) Masconomet Chieftains at (2) Peabody/Salem Tanners | McVann-O'Keefe Skating Rink |
| February 12, 2022 | (1) Masconomet Chieftains at (1) Lynnfield Pioneers | McVann-O'Keefe Skating Rink |
| February 13, 2022 | (1) Saugus Sachems at (3) Masconomet Chieftains | Haverhill Valley Forum |
| February 17, 2022 | (2) Masconomet Chieftains at (7) Winthrop Vikings | Larsen Rink |
| February 19, 2022 | (2) Andover Golden Warriors at (2) Masconomet Chieftains | Haverhill Valley Forum |
| February 21, 2022 | (3) Masconomet Chieftains at (4) St. John's Prep Eagles | Essex Sports Center |
| March 03, 2022 | (2) Hopkinton Hillers at (6) Masconomet Chieftains
Boys Division 2 Tournament |
Haverhill Valley Forum |
| March 07, 2022 | (1) Quincy Presidents at (5) Masconomet Chieftains
Boys Division 2 Tournament |
Haverhill Valley Forum |
| March 11, 2022 | (3) Duxbury Dragons at (2) Masconomet Chieftains
Boys Division 2 Tournament |
Chelmsford Forum |
