[2] Ayr 2-0 Dundee Utd [1] 2019-09-14 14:00
Stadium: Somerset Park Round: 5
Referee: Robert Madden Home Manager: Ian McCall Away Manager: Robbie Neilson
Head to Head
| Scotland Championship | 2019/04/12 18:05 | Dundee Utd v Ayr | L | 2-1 |
| Scotland Championship | 2019/01/25 19:45 | Ayr v Dundee Utd | W | 1-0 |
| Scotland Championship | 2018/11/30 19:45 | Dundee Utd v Ayr | W | 0-5 |
| Scotland Championship | 2018/10/06 14:00 | Ayr v Dundee Utd | W | 2-0 |
| Scotland Championship | 2017/04/15 16:15 | Ayr v Dundee Utd | D | 0-0 |
| Scotland Championship | 2017/03/28 18:45 | Dundee Utd v Ayr | L | 2-1 |
| Scotland Championship | 2016/12/10 15:00 | Ayr v Dundee Utd | L | 0-1 |
| Scotland Championship | 2016/08/20 14:00 | Dundee Utd v Ayr | L | 3-0 |
Home History
| Scotland League Challenge Cup | 2019/09/07 14:00 | Wrexham v Ayr | L | 7-6 |
| Scotland Championship | 2019/08/31 14:00 | Partick v Ayr | W | 2-3 |
| Scotland Championship | 2019/08/24 14:00 | Ayr v Queen of South | W | 1-0 |
| Scotland Championship | 2019/08/10 14:00 | Dundee v Ayr | L | 1-0 |
| Scotland Championship | 2019/08/03 14:00 | Ayr v Morton | W | 4-2 |
| Scotland League Cup | 2019/07/27 14:00 | Ayr v Stranraer | L | 7-8 |
| Scotland League Cup | 2019/07/20 14:00 | Ayr v Falkirk | W | 2-1 |
| Scotland League Cup | 2019/07/16 18:45 | Livingston v Ayr | L | 2-1 |
Away History
| Scotland League Challenge Cup | 2019/09/07 14:00 | Dundee Utd v Arbroath | L | 3-4 |
| Scotland Championship | 2019/08/30 18:45 | Dundee Utd v Dundee | W | 6-2 |
| Scotland Championship | 2019/08/24 14:00 | Dunfermline v Dundee Utd | W | 0-2 |
| Scotland Championship | 2019/08/09 18:05 | Partick v Dundee Utd | W | 1-2 |
| Scotland Championship | 2019/08/03 14:00 | Dundee Utd v Inverness CT | W | 4-1 |
| Club Friendly List | 2019/07/27 14:00 | Shrewsbury v Dundee Utd | L | 2-1 |
| Scotland League Cup | 2019/07/23 18:45 | Dundee Utd v East Fife | L | 0-2 |
| Scotland League Cup | 2019/07/19 18:45 | Dundee Utd v Cowdenbeath | W | 3-0 |