| | | |
| March 14, 2026 | W | Portland Hearts of Pine 3 at New York Cosmos 1 | Final |
| March 21, 2026 | T | Portland Hearts of Pine 0 at AV Alta FC 0 | Final |
| March 28, 2026 | L | Portland Hearts of Pine 0 at Sarasota Paradise 1 | Final |
| April 11, 2026 | T | One Knoxville SC 0 at Portland Hearts of Pine 0 | Final |
| April 19, 2026 | T | FC Naples 1 at Portland Hearts of Pine 1 | Final |
| April 25, 2026 | T | Portland Hearts of Pine 2 at Westchester SC 2 (USL Cup) | Final (PK 4-5) |
| May 2, 2026 | W | New York Cosmos 1 at Portland Hearts of Pine 3 | Final |
| May 6, 2026 | L | Portland Hearts of Pine 0 at Fort Wayne FC 3 | Final |
| May 9, 2026 | T | Portland Hearts of Pine 2 at Union Omaha 2 | Final |
| May 16, 2026 | W | Rhode Island FC 1 at Portland Hearts of Pine 2 (USL Cup) | Final |
| May 23, 2026 | T | Greenville Triumph SC 1 at Portland Hearts of Pine 1 | Final |
| May 30, 2026 | W | Spokane Velocity FC 1 at Portland Hearts of Pine 2 | Final |
| June 3, 2026 | L | Portland Hearts of Pine 2 at Corpus Christi FC 3 | Final |
| June 7, 2026 | L | Portland Hearts of Pine 1 at Brooklyn FC 5 (USL Cup) | Final |
| June 13, 2026 | L | Chattanooga Red Wolves SC 2 at Portland Hearts of Pine 1 | Final |
| June 19, 2026 | L | Portland Hearts of Pine 1 at Westchester SC 5 | Final |
| June 24, 2026 | W | Richmond Kickers 1 at Portland Hearts of Pine 5 | Final |
| July 3, 2026 | W | Portland Hearts of Pine 3 at FC Naples 2 | Final |
| July 11, 2026 | T | New York Cosmos 1 at Portland Hearts of Pine 1 (USL Cup) | Final (PK 2-4) |
| July 17, 2026 | L | Portland Hearts of Pine 1 at Athletic Club Boise 2 | Final |
| July 22, 2026 | | Union Omaha at Portland Hearts of Pine | 7:00 p.m. |
| August 1, 2026 | | Portland Hearts of Pine at Greenville Triumph SC | 7:00 p.m. |
| August 8, 2026 | | Corpus Christi FC at Portland Hearts of Pine | 7:00 p.m. |
| August 16, 2026 | | Forward Madison FC at Portland Hearts of Pine | 6:30 p.m. |
| August 19, 2026 | | Portland Hearts of Pine at One Knoxville SC | 7:00 p.m. |
| August 22, 2026 | | Portland Hearts of Pine at Richmond Kickers | 7:00 p.m. |
| August 29, 2026 | | Fort Wayne FC at Portland Hearts of Pine | 7:00 p.m. |
| September 2, 2026 | | Portland Hearts of Pine at Charlotte Independence | 7:30 p.m. |
| September 6, 2026 | | Westchester SC at Portland Hearts of Pine | 6:00 p.m. |
| September 13, 2026 | | AV Alta FC at Portland Hearts of Pine | 6:00 p.m. |
| September 19, 2026 | | Portland Hearts of Pine at Chattanooga Red Wolves SC | 7:00 p.m. |
| September 26, 2026 | | Sarasota Paradise at Portland Hearts of Pine | 5:00 p.m. |
| October 3, 2026 | | Portland Hearts of Pine at Spokane Velocity FC | 9:00 p.m. |
| October 10, 2026 | | Athletic Club Boise at Portland Hearts of Pine | 5:00 p.m. |
| October 17, 2026 | | Portland Hearts of Pine at Forward Madison FC | 6:00 p.m. |
| October 24, 2026 | | Charlotte Independence at Portland Hearts of Pine | 5:00 p.m. |
Portland Hearts of Pine Schedule
