| | | |
| February 28, 2026 | W | Toronto FC II 0 at Philadelphia Union II 1 | Final |
| March 8, 2026 | W | FC Cincinnati 2 0 at Philadelphia Union II 1 | Final |
| March 15, 2026 | L | Connecticut United FC 2 at Philadelphia Union II 1 | Final |
| March 22, 2026 | T | Philadelphia Union II 1 at Red Bull New York II 1 | Final (PK 4-3) |
| April 12, 2026 | W | Carolina Core FC 1 at Philadelphia Union II 4 | Final |
| April 17, 2026 | L | Philadelphia Union II 0 at Toronto FC II 1 | Final |
| April 26, 2026 | W | Philadelphia Union II 2 at Connecticut United FC 1 | Final |
| May 3, 2026 | L | Red Bull New York II 2 at Philadelphia Union II 1 | Final |
| May 13, 2026 | L | New England Revolution II 1 at Philadelphia Union II 0 | Final |
| May 17, 2026 | T | Columbus Crew 2 1 at Philadelphia Union II 1 | Final (PK 8-7) |
| May 23, 2026 | W | Atlanta United 2 1 at Philadelphia Union II 2 | Final |
| May 29, 2026 | L | Philadelphia Union II 1 at Toronto FC II 2 | Final |
| June 5, 2026 | L | Philadelphia Union II 0 at Crown Legacy FC 1 | Final |
| June 14, 2026 | | New York City FC II at Philadelphia Union II | 3:00 p.m. |
| June 21, 2026 | | Philadelphia Union II at Orlando City B | 7:00 p.m. |
| June 28, 2026 | | Philadelphia Union II at Red Bull New York II | 7:00 p.m. |
| July 5, 2026 | | Philadelphia Union II at New England Revolution II | 7:00 p.m. |
| July 12, 2026 | | Huntsville City FC at Philadelphia Union II | 3:00 p.m. |
| July 18, 2026 | | Philadelphia Union II at Columbus Crew 2 | 6:00 p.m. |
| July 25, 2026 | | Philadelphia Union II at Chattanooga FC | 7:00 p.m. |
| August 1, 2026 | | Philadelphia Union II at New York City FC II | 7:00 p.m. |
| August 8, 2026 | | FC Cincinnati 2 at Philadelphia Union II | 12:00 p.m. |
| August 16, 2026 | | Philadelphia Union II at New England Revolution II | 7:00 p.m. |
| August 23, 2026 | | Connecticut United FC at Philadelphia Union II | 3:00 p.m. |
| August 30, 2026 | | Philadelphia Union II at FC Cincinnati 2 | 6:00 p.m. |
| September 4, 2026 | | Columbus Crew 2 at Philadelphia Union II | 7:00 p.m. |
| September 13, 2026 | | Philadelphia Union II at Chicago Fire FC II | 4:00 p.m. |
| September 20, 2026 | | New York City FC II at Philadelphia Union II | 2:00 p.m. |
Philadelphia Union II Schedule
