| Sep 2, 2026 | vs Acton-BoxboroughD1 · #12 | Scrimmage | Worcester Academy - Morse Field |
| Sep 7, 2026 | vs Loomis-Chaffee | Scrimmage | Worcester Academy (FindMe Showcase) |
| Sep 7, 2026 | vs Phillips Exeter Academy | Scrimmage | Worcester Academy - Morse Field |
| Sep 12, 2026 | @ Thayer Academy | Scrimmage | |
| Sep 16, 2026 | @ Suffield Academy | W 2-0 | Suffield Academy |
| Sep 19, 2026 | vs Tabor Academy | W 5-3 | Worcester Academy - Morse Field |
| Sep 23, 2026 | @ Buckingham Browne & Nichols | W 3-2 | |
| Sep 25, 2026 | vs Mount Saint Charles Academy | | Worcester Academy - New Balance Fields |
| Sep 27, 2026 | vs Darrow | | Suffield Academy |
| Sep 30, 2026 | @ Phillips Academy Andover | L 1-2 | Smoyer Family Field, Andover |
| Oct 3, 2026 | @ Miss Porter's School | L 1-2 | Miss Porter's School |
| Oct 7, 2026 | vs Choate Rosemary Hall | W 3-0 | Worcester Academy - Morse Field |
| Oct 10, 2026 | vs Loomis-Chaffee | L 0-1 | Worcester Academy |
| Oct 17, 2026 | vs Dexter Southfield | W 1-0 | Worcester Academy South Campus and Turf Field |
| Oct 21, 2026 | vs Deerfield Academy | T 0-0 | Worcester Academy |
| Oct 24, 2026 | @ The Taft School | W 3-0 | Taft School |
| Oct 28, 2026 | vs The Pingree School | W 5-0 | Worcester Academy - New Balance Fields |
| Oct 31, 2026 | vs Milton Academy | L 1-2 | Worcester Academy - Morse Field |
| Nov 2, 2026 | @ Austin Preparatory School | T 1-1 | Upper Athletic Fields |
| Nov 4, 2026 | vs Ethel Walker School | W 5-0 | Worcester Academy - Morse Field |
| Nov 7, 2026 | vs Phillips Exeter Academy | W 2-0 | Worcester, MA |
| Nov 11, 2026 | @ St. Mark's School | W 5-0 | St. Mark's School |
| Nov 14, 2026 | @ Cushing Academy | | Cushing Academy |
| Dec 12, 2026 | vs Scorpions SC ECNL G2011/12 | | |
| Dec 13, 2026 | vs FSA FC ECNL G2011/12 | | |
| Dec 19, 2026 | vs Select ECNL G2011/12 | | |
| Feb 27, 2027 | vs FC Stars Blue ECNL G2011/12 | | |
| Mar 6, 2027 | @ Select ECNL G2011/12 | | |
| Mar 7, 2027 | @ Scorpions SC ECNL G2011/12 | | |
| Mar 13, 2027 | vs FC Stars Blue ECNL G2011/12 | | |
| Mar 20, 2027 | vs East Meadow Soccer Club ECNL G2011/12 | | |
| Mar 21, 2027 | vs SUSA FC ECNL G2011/12 | | |
| Apr 17, 2027 | vs World Class FC ECNL G2011/12 | | |
| Apr 18, 2027 | vs Connecticut FC United ECNL G2011/12 | | |
| May 1, 2027 | @ Connecticut FC United ECNL G2011/12 | | |
| May 2, 2027 | @ World Class FC ECNL G2011/12 | | |
| May 15, 2027 | @ FSA FC ECNL G2011/12 | | FSA-Farmington Sports Arena - Field 6 |
| May 22, 2027 | @ East Meadow Soccer Club ECNL G2011/12 | | East Meadow Field of Dreams - South Turf |
| May 23, 2027 | @ SUSA FC ECNL G2011/12 | | |