- 13 June 2026, Portland Hearts of Pine vs Chattanooga Red Wolves SC, 1-2, Lose
- 04 June 2026, Corpus Christi FC vs Portland Hearts of Pine, 3-2, Lose
- 30 May 2026, Portland Hearts of Pine vs Spokane Velocity FC, 2-1, Win
- 23 May 2026, Portland Hearts of Pine vs Greenville Triumph SC, 1-1, Draw
- 10 May 2026, Union Omaha vs Portland Hearts of Pine, 2-2, Draw
- 14 June 2026, Corpus Christi FC vs Richmond Kickers Chesterfield, 1-0, Lose
- 11 June 2026, AC Boise vs Richmond Kickers Chesterfield, 2-1, Lose
- 30 May 2026, Richmond Kickers Chesterfield vs AC Boise, 2-2, Draw
- 27 May 2026, Chattanooga Red Wolves SC vs Richmond Kickers Chesterfield, 5-0, Lose
- 09 May 2026, Greenville Triumph SC vs Richmond Kickers Chesterfield, 0-3, Win
Form Guide
| Lose | 1-2 | Portland Hearts of Pine vs Chattanooga Red Wolves SC | |
| Lose | 3-2 | Corpus Christi FC vs Portland Hearts of Pine | |
| Win | 2-1 | Portland Hearts of Pine vs Spokane Velocity FC | |
| Draw | 1-1 | Portland Hearts of Pine vs Greenville Triumph SC | |
| Draw | 2-2 | Union Omaha vs Portland Hearts of Pine |
- PLAYED
- 5
- WINS
- 1
- GOALS
- 8:9
- GOALS / MATCH
- 1.6
- Portland Hearts of Pine has won only one out of its last five matches with a goal difference of 8:9, scoring 1.6 goals average
| Lose | 1-0 | Corpus Christi FC vs Richmond Kickers Chesterfield | |
| Lose | 2-1 | AC Boise vs Richmond Kickers Chesterfield | |
| Draw | 2-2 | Richmond Kickers Chesterfield vs AC Boise | |
| Lose | 5-0 | Chattanooga Red Wolves SC vs Richmond Kickers Chesterfield | |
| Win | 0-3 | Greenville Triumph SC vs Richmond Kickers Chesterfield |
- PLAYED
- 5
- WINS
- 1
- GOALS
- 6:10
- GOALS / MATCH
- 1.2
- Richmond Kickers Chesterfield has won only one out of its last five matches with a goal difference of 6:10, scoring 1.2 goals average
Portland Hearts of Pine H2H Richmond Kickers Chesterfield
| Away game | Portland Hearts of Pine | 5 | 2 | Richmond Kickers Chesterfield | Home game | USL League One | |
| Home game | Portland Hearts of Pine | 0 | 0 | Richmond Kickers Chesterfield | Away game | USL League One |
- PLAYED
- 2
- WINS
- 1
- GOALS
- 5:2
- GOALS / MATCH
- 2.50
- In the last two matches that these two sides meet, Portland Hearts of Pine overtook Richmond Kickers Chesterfield once
- Portland Hearts of Pine won once and had one draw
- Teams played two times head-to-head in the current season with the goals score 5:2; average goals per match – 2.50
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