- 19 September 2026, Colchester United vs Cheltenham Town, 1-1, Draw
- 12 September 2026, Crawley Town vs Cheltenham Town, 1-3, Win
- 05 September 2026, Cheltenham Town vs Grimsby Town, 2-2, Draw
- 01 September 2026, Cheltenham Town vs York City FC, 3-2, Win
- 29 August 2026, Barnet FC vs Cheltenham Town, 2-2, Draw
- 19 September 2026, Chesterfield FC vs York City FC, 2-0, Win
- 12 September 2026, Oldham Athletic vs Chesterfield FC, 1-2, Win
- 05 September 2026, Chesterfield FC vs Barnet FC, 3-3, Draw
- 01 September 2026, Chesterfield FC vs Gillingham, 1-1, Draw
- 29 August 2026, Rotherham United vs Chesterfield FC, 2-1, Lose
Form Guide
| Draw | 1-1 | Colchester United vs Cheltenham Town | |
| Win | 1-3 | Crawley Town vs Cheltenham Town | |
| Draw | 2-2 | Cheltenham Town vs Grimsby Town | |
| Win | 3-2 | Cheltenham Town vs York City FC | |
| Draw | 2-2 | Barnet FC vs Cheltenham Town |
- PLAYED
- 5
- WINS
- 2
- GOALS
- 11:8
- GOALS / MATCH
- 2.2
- Cheltenham Town has two wins in its last five matches with a goal difference of 11:8, scoring 2.2 goals average
| Win | 2-0 | Chesterfield FC vs York City FC | |
| Win | 1-2 | Oldham Athletic vs Chesterfield FC | |
| Draw | 3-3 | Chesterfield FC vs Barnet FC | |
| Draw | 1-1 | Chesterfield FC vs Gillingham | |
| Lose | 2-1 | Rotherham United vs Chesterfield FC |
- PLAYED
- 5
- WINS
- 2
- GOALS
- 9:7
- GOALS / MATCH
- 1.8
- Chesterfield FC has two wins in its last five matches with a goal difference of 9:7, scoring 1.8 goals average
Cheltenham Town H2H Chesterfield FC
| Away game | Cheltenham Town | 0 | 1 | Chesterfield FC | Home game | League Two | |
| Home game | Cheltenham Town | 0 | 2 | Chesterfield FC | Away game | League Two | |
| Home game | Cheltenham Town | 1 | 0 | Chesterfield FC | Away game | League Two | |
| Away game | Cheltenham Town | 1 | 1 | Chesterfield FC | Home game | League Two | |
| Home game | Cheltenham Town | 1 | 1 | Chesterfield FC | Away game | League Two |
- PLAYED
- 5
- WINS
- 1
- GOALS
- 3:5
- GOALS / MATCH
- 0.60
- Cheltenham Town lost twice in head-to-head matches
- Teams played five times head-to-head in the current season with the goals score 3:5; average goals per match – 0.60
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