Darlington 2-1 Gainsborough Trinity 2019-11-23 15:00
Stadion: The Northern Echo Darlington Arena Round: 16
Head to Head
| England - National League North | 2017/12/23 15:00 | Gainsborough v Darlington 1883 | L | 3-1 |
| England - National League North | 2017/08/09 18:45 | Darlington 1883 v Gainsborough | W | 4-3 |
| England - National League North | 2017/03/25 15:00 | Gainsborough v Darlington 1883 | D | 3-3 |
| England - National League North | 2016/10/15 14:00 | Darlington 1883 v Gainsborough | W | 5-2 |
Home History
| England - FA Cup | 2019/11/20 19:45 | Darlington 1883 v Walsall | L | 0-1 |
| England - National League North | 2019/11/16 15:00 | Brackley v Darlington 1883 | L | 5-1 |
| England - FA Cup | 2019/11/09 15:00 | Walsall v Darlington 1883 | D | 2-2 |
| England - National League North | 2019/11/02 15:00 | Darlington 1883 v Hereford FC | D | 0-0 |
| England - National League North | 2019/10/30 19:45 | Darlington 1883 v Kidderminster | W | 1-0 |
| England - FA Cup - Qualifikation | 2019/10/19 14:00 | Tamworth v Darlington 1883 | W | 0-3 |
| England - National League North | 2019/10/12 14:00 | Darlington 1883 v Boston Utd | W | 2-1 |
| England - FA Cup - Qualifikation | 2019/10/05 14:00 | Leamington v Darlington 1883 | W | 0-2 |
Away History
| England - Northern Premier League | 2019/11/16 15:00 | Gainsborough v Morpeth Town | L | 0-1 |
| England - FA Trophy | 2019/11/09 15:00 | Tamworth v Gainsborough | W | 3-5 |
| England - Northern Premier League | 2019/11/02 15:00 | FC United of Manchester v Gainsborough | D | 2-2 |
| England - FA Trophy | 2019/10/29 19:46 | Dunston UTS v Gainsborough | W | 0-4 |
| England - Northern Premier League | 2019/10/19 14:00 | Ashton Utd v Gainsborough | L | 3-1 |
| England - Northern Premier League | 2019/10/15 18:45 | Gainsborough v Buxton | D | 0-0 |
| England - Northern Premier League | 2019/10/12 14:00 | Gainsborough v Atherton Collieries | L | 0-2 |
| England - Northern Premier League | 2019/10/05 14:00 | Basford Utd v Gainsborough | L | 4-3 |