Head to Head
| England League 2 | 2024/10/22 18:45 | Chesterfield v Colchester | D | 1-1 |
| England League 2 | 2017/12/30 15:00 | Chesterfield v Colchester | D | 0-0 |
| England League 2 | 2017/09/12 18:45 | Colchester v Chesterfield | D | 1-1 |
| England FA Cup | 2016/11/05 15:00 | Colchester v Chesterfield | L | 1-2 |
| England League 1 | 2016/02/16 19:45 | Colchester v Chesterfield | D | 1-1 |
| England League 1 | 2015/09/12 14:00 | Chesterfield v Colchester | D | 3-3 |
| England League 1 | 2015/04/14 18:45 | Chesterfield v Colchester | L | 6-0 |
| England League 1 | 2014/10/21 18:45 | Colchester v Chesterfield | W | 2-1 |
Home History
| England League 2 | 2025/02/08 15:00 | Colchester v Walsall | W | 2-1 |
| England League 2 | 2025/02/01 15:00 | Tranmere v Colchester | W | 1-3 |
| England League 2 | 2025/01/25 15:00 | Colchester v Morecambe | W | 1-0 |
| England League 2 | 2025/01/21 19:45 | Harrogate Town v Colchester | D | 0-0 |
| England League 2 | 2025/01/18 15:00 | Bromley v Colchester | W | 0-1 |
| England EFL Trophy | 2025/01/14 19:00 | Cheltenham v Colchester | L | 2-1 |
| England League 2 | 2025/01/04 15:00 | Colchester v Accrington Stanley | L | 0-2 |
| England League 2 | 2025/01/01 15:00 | Swindon v Colchester | L | 3-2 |
Away History
| England League 2 | 2025/02/06 19:45 | Chesterfield v Doncaster | W | 5-2 |
| England League 2 | 2025/02/01 12:30 | Cheltenham v Chesterfield | L | 1-0 |
| England League 2 | 2025/01/28 19:45 | Chesterfield v Bromley | W | 3-0 |
| England League 2 | 2025/01/25 15:00 | Chesterfield v Port Vale | D | 1-1 |
| England League 2 | 2025/01/18 15:00 | Grimsby v Chesterfield | D | 1-1 |
| England EFL Trophy | 2025/01/14 19:00 | Chesterfield v Rotherham | D | 0-0 |
| England League 2 | 2025/01/01 15:00 | Chesterfield v Milton Keynes Dons | L | 1-2 |
| England League 2 | 2024/12/29 15:00 | Bradford v Chesterfield | L | 2-1 |