Summary of previous matches between the team of AFC Wimbledon and the team of Chesterfield since 2012-08-18:
AFC Wimbledon won 2 matches against Chesterfield, lost 4 matches, and 3 matches were draws.
| Time | League | Home Team | Score | Away Team |
|---|---|---|---|---|
| 2019-08-26 | England Conference | Stockport County | 2 : 0 | Chesterfield |
| 2019-08-24 | England Conference | Chesterfield | 2 : 2 | Barrow |
| 2019-08-17 | England Conference | Barnet | 2 : 2 | Chesterfield |
| 2019-08-14 | England Conference | Chesterfield | 1 : 2 | Woking |
| 2019-08-10 | England Conference | Boreham Wood | 2 : 2 | Chesterfield |
| 2019-08-07 | England Conference | Maidenhead United | 1 : 1 | Chesterfield |
| 2019-08-03 | England Conference | Chesterfield | 1 : 2 | Dover Athletic |
| 2019-07-27 | International Club Friendly | Chesterfield | 2 : 5 | Burton Albion |
| 2019-07-25 | International Club Friendly | Sheffield FC | 2 : 1 | Chesterfield |
| 2019-07-24 | International Club Friendly | Chesterfield | 0 : 5 | Sheffield United |
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