[11] Orlando City SC 2-2 Philadelphia Union [5] 2018-09-01 23:30
Stadium: Inter&Co Stadium Round: 1
Referee: Christopher Penso Home Manager: James O'Connor Away Manager: Jim Curtin
Head to Head
| USA US Open Cup | 2018/07/18 23:00 | Philadelphia Union v Orlando City SC | L | 1-0 |
| USA MLS | 2018/04/14 00:00 | Philadelphia Union v Orlando City SC | W | 0-2 |
| USA MLS | 2017/10/22 20:00 | Philadelphia Union v Orlando City SC | L | 6-1 |
| USA MLS | 2017/03/18 23:30 | Orlando City SC v Philadelphia Union | W | 2-1 |
| USA MLS | 2016/10/16 19:00 | Philadelphia Union v Orlando City SC | W | 0-2 |
| USA MLS | 2016/05/25 23:30 | Orlando City SC v Philadelphia Union | D | 2-2 |
| USA MLS | 2016/04/08 23:00 | Philadelphia Union v Orlando City SC | L | 2-1 |
| USA MLS | 2015/10/25 21:00 | Philadelphia Union v Orlando City SC | L | 1-0 |
| USA MLS | 2015/08/08 23:30 | Orlando City SC v Philadelphia Union | D | 0-0 |
| Club Friendly List | 2014/02/19 23:00 | Orlando City SC v Philadelphia Union | D | 1-1 |