Home History
| England National League South | 2019/09/14 14:00 | Dorking Wanderers v Maidstone Utd | L | 3-1 |
| England National League South | 2019/09/07 14:00 | Maidstone Utd v Havant and W | D | 2-2 |
| England National League South | 2019/09/03 18:45 | Dulwich v Maidstone Utd | W | 0-1 |
| England National League South | 2019/08/31 14:00 | Wealdstone v Maidstone Utd | L | 2-1 |
| England National League South | 2019/08/26 14:00 | Maidstone Utd v Chelmsford | W | 4-1 |
| England National League South | 2019/08/24 14:00 | Concord Rangers v Maidstone Utd | W | 0-1 |
| England National League South | 2019/08/17 14:00 | Maidstone Utd v Slough | D | 1-1 |
| England National League South | 2019/08/13 18:45 | Maidstone Utd v Eastbourne Borough | D | 0-0 |
Away History
| England Isthmian Premier Division | 2019/09/17 18:45 | Bognor Regis Town v Cheshunt | W | 1-2 |
| England Isthmian Premier Division | 2019/09/14 14:00 | Cheshunt v Margate | L | 1-2 |
| England FA Cup Qualification | 2019/09/07 14:00 | Cheshunt v Brightlingsea Regent | W | 1-0 |
| England Isthmian Premier Division | 2019/08/31 14:00 | Bishop's Stortford v Cheshunt | L | 3-2 |
| England Isthmian Premier Division | 2019/08/26 14:00 | Cheshunt v Corinthian Casuals | D | 1-1 |
| England Isthmian Premier Division | 2019/08/17 14:00 | Cheshunt v Haringey Borough | L | 0-1 |
| England Isthmian Premier Division | 2019/08/13 18:45 | Cheshunt v Potters Bar Town | W | 2-0 |
| England Isthmian Premier Division | 2019/08/10 14:00 | East Thurrock v Cheshunt | L | 4-1 |