- 29 August 2026, Portland Hearts of Pine vs Fort Wayne FC, 1-4, Lose
- 22 August 2026, Richmond Kickers Chesterfield vs Portland Hearts of Pine, 1-1, Draw
- 19 August 2026, One Knoxville SC vs Portland Hearts of Pine, 1-1, Draw
- 16 August 2026, Portland Hearts of Pine vs Forward Madison FC, 1-2, Lose
- 08 August 2026, Portland Hearts of Pine vs Corpus Christi FC, 0-2, Lose
- 29 August 2026, Westchester SC vs Spokane Velocity FC, 1-3, Lose
- 23 August 2026, Corpus Christi FC vs Westchester SC, 2-2, Draw
- 15 August 2026, Westchester SC vs FC Naples, 3-2, Win
- 02 August 2026, Forward Madison FC vs Westchester SC, 2-0, Lose
- 26 July 2026, AV Alta FC vs Westchester SC, 0-0, Draw
Form Guide
| Lose | 1-4 | Portland Hearts of Pine vs Fort Wayne FC | |
| Draw | 1-1 | Richmond Kickers Chesterfield vs Portland Hearts of Pine | |
| Draw | 1-1 | One Knoxville SC vs Portland Hearts of Pine | |
| Lose | 1-2 | Portland Hearts of Pine vs Forward Madison FC | |
| Lose | 0-2 | Portland Hearts of Pine vs Corpus Christi FC |
- PLAYED
- 5
- WINS
- 0
- GOALS
- 4:10
- GOALS / MATCH
- 0.8
- Portland Hearts of Pine has lost three matches in a row with a goal difference of 4:10, scoring 0.8 goals average
| Lose | 1-3 | Westchester SC vs Spokane Velocity FC | |
| Draw | 2-2 | Corpus Christi FC vs Westchester SC | |
| Win | 3-2 | Westchester SC vs FC Naples | |
| Lose | 2-0 | Forward Madison FC vs Westchester SC | |
| Draw | 0-0 | AV Alta FC vs Westchester SC |
- PLAYED
- 5
- WINS
- 1
- GOALS
- 6:9
- GOALS / MATCH
- 1.2
- Westchester SC has won only one out of its last five matches with a goal difference of 6:9, scoring 1.2 goals average
Portland Hearts of Pine H2H Westchester SC
| Away game | Portland Hearts of Pine | 1 | 5 | Westchester SC | Home game | USL League One | |
| Away game | Portland Hearts of Pine | 6 | 7 | Westchester SC | Home game | USL Cup | |
| Home game | Portland Hearts of Pine | 2 | 2 | Westchester SC | Away game | USL League One | |
| Away game | Portland Hearts of Pine | 3 | 2 | Westchester SC | Home game | USL League One |
- PLAYED
- 4
- WINS
- 1
- GOALS
- 12:16
- GOALS / MATCH
- 3.00
- Portland Hearts of Pine lost twice in head-to-head matches
- Teams played four times head-to-head in the current season with the goals score 12:16; average goals per match – 3.00
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