Head to Head
| England League 1 | 2016/03/28 14:00 | Oldham v Chesterfield | W | 1-0 |
| England League 1 | 2015/11/14 15:00 | Chesterfield v Oldham | W | 1-2 |
| England League 1 | 2015/04/18 14:00 | Oldham v Chesterfield | D | 0-0 |
| England League 1 | 2014/10/18 14:00 | Chesterfield v Oldham | D | 1-1 |
Home History
| England League 1 | 2016/09/03 14:00 | Oldham v Shrewsbury | L | 2-3 |
| England EFL Trophy | 2016/08/30 18:45 | Oldham v Carlisle | L | 4-5 |
| England League 1 | 2016/08/27 14:00 | Bradford v Oldham | D | 1-1 |
| England EFL Cup | 2016/08/23 18:45 | Preston v Oldham | L | 2-0 |
| England League 1 | 2016/08/20 14:00 | Bury v Oldham | W | 0-1 |
| England League 1 | 2016/08/16 18:45 | Oldham v Northampton | D | 0-0 |
| England League 1 | 2016/08/13 14:00 | Oldham v Walsall | D | 0-0 |
| England EFL Cup | 2016/08/09 18:45 | Oldham v Wigan | W | 2-1 |
Away History
| England League 1 | 2016/09/03 14:00 | AFC Wimbledon v Chesterfield | L | 2-1 |
| England EFL Trophy | 2016/08/30 18:45 | Chesterfield v Wolverhampton U23 | W | 2-1 |
| England League 1 | 2016/08/27 14:00 | Chesterfield v Millwall | L | 1-3 |
| England League 1 | 2016/08/20 14:00 | Shrewsbury v Chesterfield | L | 2-1 |
| England League 1 | 2016/08/16 18:45 | Chesterfield v Walsall | W | 2-0 |
| England League 1 | 2016/08/13 14:00 | Chesterfield v Swindon | W | 3-1 |
| England EFL Cup | 2016/08/09 18:45 | Rochdale v Chesterfield | L | 3-1 |
| England League 1 | 2016/08/06 14:00 | Oxford Utd v Chesterfield | D | 1-1 |