| | | |
| March 7, 2026 | L | One Knoxville SC 3 at Westchester SC 2 | Final |
| March 14, 2026 | T | Charlotte Independence 1 at Westchester SC 1 | Final |
| March 29, 2026 | L | Westchester SC 2 at Greenville Triumph SC 4 | Final |
| April 4, 2026 | W | Corpus Christi FC 1 at Westchester SC 5 | Final |
| April 8, 2026 | W | Sarasota Paradise 0 at Westchester SC 2 | Final |
| April 18, 2026 | L | Westchester SC 0 at Athletic Club Boise 4 | Final |
| April 25, 2026 | T | Portland Hearts of Pine 2 at Westchester SC 2 (USL Cup) | Final (PK 4-5) |
| May 1, 2026 | L | Westchester SC 0 at Richmond Kickers 1 | Final |
| May 9, 2026 | L | Westchester SC 0 at Fort Wayne FC 1 | Final |
| May 15, 2026 | L | New York Cosmos 3 at Westchester SC 2 (USL Cup) | Final |
| May 23, 2026 | L | Westchester SC 0 at FC Naples 1 | Final |
| June 6, 2026 | | Westchester SC at Rhode Island FC (USL Cup) | 6:30 p.m. |
| June 10, 2026 | | Fort Wayne FC at Westchester SC | 7:00 p.m. |
| June 14, 2026 | | Greenville Triumph SC at Westchester SC | 7:00 p.m. |
| June 19, 2026 | | Portland Hearts of Pine at Westchester SC | 7:00 p.m. |
| June 24, 2026 | | Westchester SC at Spokane Velocity FC | 9:00 p.m. |
| July 1, 2026 | | Westchester SC at Chattanooga Red Wolves SC | 7:00 p.m. |
| July 5, 2026 | | Athletic Club Boise at Westchester SC | 7:00 p.m. |
| July 11, 2026 | | Westchester SC at Hartford Athletic (USL Cup) | 6:00 p.m. |
| July 18, 2026 | | Westchester SC at Union Omaha | 8:00 p.m. |
| July 22, 2026 | | New York Cosmos at Westchester SC | 7:00 p.m. |
| July 25, 2026 | | Westchester SC at AV Alta FC | 11:00 p.m. |
| August 1, 2026 | | Westchester SC at Forward Madison FC | 8:00 p.m. |
| August 15, 2026 | | FC Naples at Westchester SC | 7:00 p.m. |
| August 22, 2026 | | Westchester SC at Corpus Christi FC | 8:30 p.m. |
| August 29, 2026 | | Spokane Velocity FC at Westchester SC | 7:00 p.m. |
| September 2, 2026 | | Chattanooga Red Wolves SC at Westchester SC | 7:00 p.m. |
| September 6, 2026 | | Westchester SC at Portland Hearts of Pine | 6:00 p.m. |
| September 12, 2026 | | Westchester SC at Charlotte Independence | 7:00 p.m. |
| September 16, 2026 | | Richmond Kickers at Westchester SC | 7:00 p.m. |
| September 19, 2026 | | Westchester SC at New York Cosmos | 5:00 p.m. |
| September 27, 2026 | | Westchester SC at One Knoxville SC | 3:00 p.m. |
| October 3, 2026 | | AV Alta FC at Westchester SC | 7:00 p.m. |
| October 10, 2026 | | Forward Madison FC at Westchester SC | 7:00 p.m. |
| October 17, 2026 | | Union Omaha at Westchester SC | 7:00 p.m. |
| October 24, 2026 | | Westchester SC at Sarasota Paradise | 7:30 p.m. |
Westchester SC Schedule
