All countries
| Pittsburgh | Detroit | 2:1 (1:0, 1:1) | details | 19.04.2026 | ||||
| 1/16-finals | New York Red Bulls | Pittsburgh | 3:1 (2:0, 1:1) | details | 16.04.2026 | |||
| Birmingham | Pittsburgh | 1:0 (1:0, 0:0) | details | 12.04.2026 | ||||
| Indy Eleven | Pittsburgh | 1:1 (1:0, 0:1) | details | 05.04.2026 | ||||
| 1/32-finals | Pittsburgh | Virginia Dream | 2:0 (0:0, 2:0) | details | 01.04.2026 | |||
| Pittsburgh | Sporting Jax | 3:2 (2:0, 1:2) | details | 29.03.2026 | ||||
| 1/64-finals | Pittsburgh | Steel City | 2:1 (1:0, 1:1) | details | 26.03.2026 | |||
| Tampa Bay | Pittsburgh | 3:0 (1:0, 2:0) | details | 22.03.2026 | ||||
| Loudoun | Pittsburgh | 2:3 (1:1, 1:2) | details | 14.03.2026 | ||||
| Charleston | Pittsburgh | 2:1 (1:0, 1:1) | details | 08.03.2026 | ||||
| Pittsburgh | Lexington | 1:2 (1:0, 0:2) | details | 21.02.2026 | ||||
| Pittsburgh | Loudoun | 2:1 (1:0, 1:1) | details | 13.02.2026 | ||||
| Indy Eleven | Pittsburgh | 0:3 (0:2, 0:1) | details | 06.02.2026 | ||||
| Pittsburgh | Richmond Kickers | 2:0 (0:0, 2:0) | details | 02.02.2026 | ||||
| Final | FC Tulsa | Pittsburgh | 0:1 AfP (0:0, 0:0, 0:0, 3:5) | details | 22.11.2025 | |||
| Semi-finals | Pittsburgh | Rhode Island | 1:0 (0:0, 1:0) | details | 16.11.2025 | |||
| Quarter-finals | Pittsburgh | Detroit | 1:0 AfP (0:0, 0:0, 0:0, 4:3) | details | 09.11.2025 | |||
| 1/8-finals | Pittsburgh | Hartford Athletic | 1:0 AfP (0:0, 0:0, 0:0, 4:2) | details | 01.11.2025 | |||
| Pittsburgh | Phoenix Rising | 0:0 (0:0, 0:0) | details | 26.10.2025 | ||||
| Monterey Bay | Pittsburgh | 0:3 (0:1, 0:2) | details | 19.10.2025 | ||||
| Pittsburgh | Indy Eleven | 2:1 (1:0, 1:1) | details | 12.10.2025 | ||||
| Miami FC | Pittsburgh | 3:1 (0:1, 3:0) | details | 05.10.2025 | ||||
| Pittsburgh | Las Vegas Lights | 1:0 (1:0, 0:0) | details | 29.09.2025 | ||||
| Hartford Athletic | Pittsburgh | 1:2 (1:1, 0:1) | details | 21.09.2025 | ||||
| Pittsburgh | Louisville City | 0:2 (0:0, 0:2) | details | 14.09.2025 | ||||
| Oakland Roots | Pittsburgh | 0:2 (0:2, 0:0) | details | 07.09.2025 | ||||
| Tampa Bay | Pittsburgh | 2:1 (0:1, 2:0) | details | 31.08.2025 | ||||
| Birmingham | Pittsburgh | 1:1 (1:0, 0:1) | details | 24.08.2025 | ||||
| Pittsburgh | Charleston | 1:2 (1:1, 0:1) | details | 17.08.2025 | ||||
| Pittsburgh | Orange County SC | 1:1 (0:1, 1:0) | details | 10.08.2025 | ||||
| Pittsburgh | Rhode Island | 2:0 (0:0, 2:0) | details | 03.08.2025 | ||||
| Pittsburgh | Miami FC | 1:1 (0:0, 1:1) | details | 30.07.2025 | ||||
| Group 4 | Portland Hearts of Pine | Pittsburgh | 3:2 AfP (0:0, 2:2, 5:4) | details | 26.07.2025 | |||
| Detroit | Pittsburgh | 0:0 (0:0, 0:0) | details | 19.07.2025 | ||||
| Pittsburgh | Loudoun | 2:2 (1:1, 1:1) | details | 13.07.2025 | ||||
| Pittsburgh | New Mexico | 1:0 (0:0, 1:0) | details | 05.07.2025 | ||||
| Group 4 | Pittsburgh | Westchester SC | 1:0 (1:0, 0:0) | details | 29.06.2025 | |||
| Pittsburgh | Tampa Bay | 2:1 (2:1, 0:0) | details | 22.06.2025 | ||||
| Indy Eleven | Pittsburgh | 1:0 (1:0, 0:0) | details | 15.06.2025 | ||||
| Pittsburgh | Detroit | 2:0 (1:0, 1:0) | details | 08.06.2025 | ||||
| Group 4 | Pittsburgh | Rhode Island | 0:1 (0:1, 0:0) | details | 01.06.2025 | |||
| Rhode Island | Pittsburgh | 0:1 (0:1, 0:0) | details | 24.05.2025 | ||||
| 1/8-finals | Philadelphia Union | Pittsburgh | 4:1 (2:0, 2:1) | details | 22.05.2025 | |||
| Colorado Springs | Pittsburgh | 1:0 (1:0, 0:0) | details | 18.05.2025 | ||||
| Louisville City | Pittsburgh | 0:0 (0:0, 0:0) | details | 11.05.2025 | ||||
| 1/16-finals | Pittsburgh | New York City | 1:0 (0:0, 1:0) | details | 08.05.2025 | |||
| Pittsburgh | North Carolina | 0:2 (0:0, 0:2) | details | 04.05.2025 | ||||
| Group 4 | Detroit | Pittsburgh | 1:0 (0:0, 1:0) | details | 26.04.2025 | |||
| Loudoun | Pittsburgh | 2:1 (1:0, 1:1) | details | 19.04.2025 | ||||
| 1/32-finals | Columbus Crew 2 | Pittsburgh | 0:1 (0:1, 0:0) | details | 16.04.2025 | |||