| Date | Match | League | Result | OU 2.5 | Both to score |
|---|---|---|---|---|---|
| 9/19/26 | Chesterfield vs York City | League Two | 2:0 | No | No |
| 3/29/24 | York City vs Chesterfield | Blue Square Premier | 2:1 | Yes | Yes |
| 10/24/23 | Chesterfield vs York City | Blue Square Premier | 4:0 | Yes | No |
| 4/7/23 | Chesterfield vs York City | Blue Square Premier | 1:3 | Yes | Yes |
| 10/25/22 | York City vs Chesterfield | Blue Square Premier | 1:1 | No | Yes |
| 1/28/14 | York City vs Chesterfield | League Two | 0:2 | No | No |
| 10/22/13 | Chesterfield vs York City | League Two | 2:2 | Yes | Yes |
| 12/26/12 | Chesterfield vs York City | League Two | 3:0 | Yes | No |
| 9/8/12 | York City vs Chesterfield | League Two | 2:2 | Yes | Yes |