| | | |
| March 29, 2025 | T | Portland Hearts of Pine 0 at FC Naples 0 | Final |
| April 5, 2025 | T | Portland Hearts of Pine 0 at Spokane Velocity FC 0 | Final |
| April 12, 2025 | L | Portland Hearts of Pine 1 at South Georgia Tormenta FC 2 | Final |
| April 26, 2025 | L | Portland Hearts of Pine 0 at Hartford Athletic 2 (Jagermeister Cup) | Final |
| May 4, 2025 | T | One Knoxville SC 1 at Portland Hearts of Pine 1 | Final |
| May 10, 2025 | T | Portland Hearts of Pine 2 at Union Omaha 2 | Final |
| May 17, 2025 | W | FC Naples 1 at Portland Hearts of Pine 2 | Final |
| May 24, 2025 | T | Portland Hearts of Pine 1 at Forward Madison FC 1 | Final |
| May 31, 2025 | W | Detroit City FC 2 at Portland Hearts of Pine 4 (Jagermeister Cup) | Final |
| June 7, 2025 | L | Portland Hearts of Pine 1 at Chattanooga Red Wolves SC 2 | Final |
| June 15, 2025 | W | Union Omaha 1 at Portland Hearts of Pine 3 | Final |
| June 21, 2025 | T | Portland Hearts of Pine 1 at AV Alta FC 1 | Final |
| June 27, 2025 | L | Portland Hearts of Pine 1 at Rhode Island FC 4 (Jagermeister Cup) | Final |
| July 2, 2025 | L | AV Alta FC 2 at Portland Hearts of Pine 0 | Final |
| July 6, 2025 | T | South Georgia Tormenta FC 1 at Portland Hearts of Pine 1 | Final |
| July 12, 2025 | W | Portland Hearts of Pine 1 at Texoma FC 0 | Final |
| July 16, 2025 | W | Greenville Triumph SC 1 at Portland Hearts of Pine 3 | Final |
| July 19, 2025 | T | Portland Hearts of Pine 1 at Charlotte Independence 1 | Final |
| July 25, 2025 | T | Pittsburgh Riverhounds SC 2 at Portland Hearts of Pine 2 (Jagermeister Cup) | Final |
| August 2, 2025 | L | Portland Hearts of Pine 0 at One Knoxville SC 1 | Final |
| August 9, 2025 | T | Richmond Kickers 0 at Portland Hearts of Pine 0 | Final |
| August 17, 2025 | | Spokane Velocity FC at Portland Hearts of Pine | Ppd. |
| August 24, 2025 | W | Portland Hearts of Pine 3 at Westchester SC 2 | Final |
| August 30, 2025 | W | Charlotte Independence 2 at Portland Hearts of Pine 4 | Final |
| September 3, 2025 | W | Portland Hearts of Pine 3 at Greenville Triumph SC 2 | Final |
| September 13, 2025 | T | Chattanooga Red Wolves SC 1 at Portland Hearts of Pine 1 | Final |
| September 17, 2025 | W | Portland Hearts of Pine 5 at Richmond Kickers 2 | Final |
| September 21, 2025 | W | FC Naples 0 at Portland Hearts of Pine 1 | Final |
| September 27, 2025 | W | Texoma FC 0 at Portland Hearts of Pine 1 | Final |
| October 1, 2025 | L | Portland Hearts of Pine 0 at Union Omaha 1 | Final |
| October 4, 2025 | L | Forward Madison FC 3 at Portland Hearts of Pine 1 | Final |
| October 10, 2025 | L | Portland Hearts of Pine 1 at One Knoxville SC 3 | Final |
| October 18, 2025 | T | Westchester SC 2 at Portland Hearts of Pine 2 | Final |
| October 21, 2025 | W | Spokane Velocity FC 1 at Portland Hearts of Pine 6 | Final |
| October 25, 2025 | T | AV Alta FC 2 at Portland Hearts of Pine 2 | Final |
| November 1, 2025 | W | Portland Hearts of Pine 1 at Chattanooga Red Wolves SC 0 (Playoff) | Final |
| November 9, 2025 | T | Portland Hearts of Pine 2 at Spokane Velocity FC 2 (Playoff) | Final (PK 5-6) |
Portland Hearts of Pine Schedule
