[5] Dunfermline 2-2 Dundee [3] 2019-08-02 18:05
Stadium: East End Park Round: 1
Referee: Greg Aitken Home Manager: Stevie Crawford Away Manager: James McPake
Head to Head
| Scotland League Cup | 2018/07/22 14:00 | Dundee v Dunfermline | W | 0-1 |
| Scotland League Cup | 2015/08/25 18:45 | Dunfermline v Dundee | W | 3-1 |
Home History
| Scotland League Cup | 2019/07/27 14:00 | Dunfermline v East Kilbride | W | 4-0 |
| Scotland League Cup | 2019/07/20 14:00 | FC Edinburgh v Dunfermline | L | 1-0 |
| Scotland League Cup | 2019/07/17 18:45 | Dunfermline v Albion | W | 6-0 |
| Scotland League Cup | 2019/07/14 14:00 | St Mirren v Dunfermline | W | 2-3 |
| UK Friendlies | 2019/07/10 18:46 | Kelty Hearts v Dunfermline | W | 0-3 |
| Club Friendly List | 2019/07/06 14:00 | Dunfermline v Hibernian | L | 1-3 |
| Club Friendly List | 2019/06/29 13:00 | Forfar v Dunfermline | W | 0-1 |
| Scotland Championship | 2019/05/04 14:00 | Inverness CT v Dunfermline | L | 1-0 |
Away History
| Scotland League Cup | 2019/07/28 14:00 | Dundee v Inverness CT | W | 1-0 |
| Scotland League Cup | 2019/07/20 14:00 | Dundee v Peterhead | W | 4-2 |
| Scotland League Cup | 2019/07/17 18:45 | Cove Rangers v Dundee | W | 2-3 |
| Scotland League Cup | 2019/07/13 14:00 | Raith v Dundee | W | 0-3 |
| Club Friendly List | 2019/07/09 18:45 | Dundee v Blackpool | W | 1-0 |
| Club Friendly List | 2019/07/05 10:00 | Dundee v Scunthorpe | L | 1-2 |
| Club Friendly List | 2019/07/02 16:30 | Nottm Forest v Dundee | D | 0-0 |
| Club Friendly List | 2019/06/29 12:00 | Brechin v Dundee | W | 1-2 |