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 |
|---|---|---|---|---|
| 2020-12-02 | England Conference | Chesterfield | 0 : 0 | Aldershot Town |
| 2020-11-28 | England Conference | Weymouth | 1 : 2 | Chesterfield |
| 2020-11-21 | England Conference | Chesterfield | 2 : 3 | Notts County |
| 2020-11-18 | England Conference | Altrincham | 3 : 2 | Chesterfield |
| 2020-11-14 | England Conference | Chesterfield | 1 : 2 | Maidenhead United |
| 2020-11-05 | England FA Cup | Stockport County | 4 : 0 | Chesterfield |
| 2020-10-31 | England Conference | Yeovil Town | 0 : 1 | Chesterfield |
| 2020-10-24 | England FA Cup | Stockport County | 1 : 1 | Chesterfield |
| 2020-10-21 | England Conference | Wealdstone FC | 3 : 2 | Chesterfield |
| 2020-10-18 | England Conference | Chesterfield | 1 : 2 | Stockport County |
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