Summary of previous matches between the team of Cheltenham Town and the team of Chesterfield since 2006-11-18:
Cheltenham Town won 3 matches against Chesterfield, lost 8 matches, and 4 matches were draws.
| Time | League | Home Team | Score | Away Team |
|---|---|---|---|---|
| 2025-07-26 | International Club Friendly | Chesterfield | 1 : 4 | Sheffield United |
| 2025-07-19 | International Club Friendly | Alfreton Town | 1 : 1 | Chesterfield |
| 2025-07-12 | International Club Friendly | Chesterfield | 0 : 0 | Nottingham Forest |
| 2025-07-09 | International Club Friendly | Chesterfield | 5 : 0 | Burton Albion |
| 2025-07-05 | International Club Friendly | Matlock Town | 2 : 1 | Chesterfield |
| 2025-05-03 | England League 2 | Accrington Stanley | 0 : 1 | Chesterfield |
| 2025-04-26 | England League 2 | Chesterfield | 4 : 1 | Morecambe |
| 2025-04-21 | England League 2 | Chesterfield | 3 : 3 | Bradford City |
| 2025-04-18 | England League 2 | AFC Wimbledon | 0 : 0 | Chesterfield |
| 2025-04-12 | England League 2 | Chesterfield | 3 : 0 | Fleetwood Town |
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