- 26 September 2026, Cheltenham Town vs Chesterfield FC, 2-1, Win
- 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
- 26 September 2026, Cheltenham Town vs Chesterfield FC, 2-1, Lose
- 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
Cheltenham Town narrowly edged out Chesterfield FC with a 1-0 victory, capitalizing on a decisive moment well into the second half. Cheltenham’s single goal, scored at 1:31:56, was the product of persistent offensive pressure that paid off despite their fewer shots on target compared to Chesterfield. The goal was a testament to their ability to convert when it mattered most, showcasing their clinical edge in front of the goal.
The match was a tale of contrasting styles, with Chesterfield dictating much of the pace through their aggressive approach and higher number of corner kicks, totaling eight compared to Cheltenham's two. Despite their dominance in set-pieces, Chesterfield struggled to convert their opportunities into tangible results. Cheltenham's defense held firm, managing to keep Chesterfield at bay while avoiding the pitfalls of defensive errors, as indicated by their four offsides which disrupted potential scoring opportunities for the visitors.
Disciplinary issues played a notable role in Chesterfield's inability to break through. They accrued three yellow cards, two of which came in the first half, disrupting their flow and possibly impacting their aggressive pursuit of a goal. Cheltenham's two yellow cards in the second half did little to impede their strategic focus, indicating a more composed handling of the game’s physicality. This discipline allowed Cheltenham to absorb pressure and strategically counter Chesterfield’s advances, ultimately leading to their narrow but deserved win.
Form Guide
| Win | 2-1 | Cheltenham Town vs Chesterfield FC | |
| 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 |
- PLAYED
- 5
- WINS
- 3
- GOALS
- 11:7
- GOALS / MATCH
- 2.2
- Cheltenham Town has won three out of its last five matches with a goal difference of 11:7, scoring 2.2 goals average
| Lose | 2-1 | Cheltenham Town vs Chesterfield FC | |
| 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 |
- 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
| Home game | Cheltenham Town | 2 | 1 | Chesterfield FC | Away game | League Two | |
| 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 |
- PLAYED
- 5
- WINS
- 2
- GOALS
- 4:5
- GOALS / MATCH
- 0.80
- In the last five matches that these two sides meet, Cheltenham Town overtook Chesterfield FC twice
- Cheltenham Town won twice, lost twice and had one draw
- Teams played five times head-to-head in the current season with the goals score 4:5; average goals per match – 0.80
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