[10] Darlington 2-1 Gloucester City [18] 2020-01-04 15:00
Stadium: The Northern Echo Darlington Arena Round: 25
Head to Head
| England National League North | 2019/09/07 14:00 | Gloucester v Darlington 1883 | L | 2-1 |
| England National League North | 2017/01/14 15:00 | Darlington 1883 v Gloucester | W | 2-0 |
| England National League North | 2016/08/21 14:00 | Gloucester v Darlington 1883 | W | 1-2 |
Home History
| England National League North | 2020/01/01 15:00 | Spennymoor Town v Darlington 1883 | L | 3-1 |
| England National League North | 2019/12/28 15:00 | Blyth Spartans v Darlington 1883 | W | 0-2 |
| England National League North | 2019/12/26 15:00 | Darlington 1883 v Spennymoor Town | W | 2-1 |
| England National League North | 2019/12/21 15:00 | York v Darlington 1883 | W | 0-1 |
| England FA Trophy | 2019/12/14 15:00 | Solihull Moors v Darlington 1883 | D | 2-2 |
| England National League North | 2019/12/07 15:00 | Darlington 1883 v Chester | W | 2-0 |
| England National League North | 2019/12/03 19:45 | Leamington v Darlington 1883 | L | 3-0 |
| England National League North | 2019/11/30 15:00 | Darlington 1883 v AFC Telford | L | 2-3 |
Away History
| England National League North | 2020/01/01 15:00 | Gloucester v Leamington | W | 2-1 |
| England National League North | 2019/12/28 15:00 | Gloucester v AFC Telford | L | 0-1 |
| England National League North | 2019/12/26 15:00 | Leamington v Gloucester | L | 3-0 |
| England National League North | 2019/12/07 15:00 | Southport v Gloucester | L | 1-0 |
| England National League North | 2019/11/30 15:00 | Gloucester v Kettering | D | 2-2 |
| England FA Trophy | 2019/11/24 15:00 | Gloucester v Bradford P A | L | 0-2 |
| England National League North | 2019/11/09 15:00 | Farsley Celtic v Gloucester | D | 1-1 |
| England National League North | 2019/11/02 15:00 | Gloucester v Curzon Ashton | D | 2-2 |