[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 |
Home History
| USA MLS | 2018/08/25 00:00 | Orlando City SC v Atlanta United | L | 1-2 |
| USA MLS | 2018/08/13 00:00 | DC United v Orlando City SC | L | 3-2 |
| USA MLS | 2018/08/04 23:30 | Orlando City SC v New England Revolution | D | 3-3 |
| USA MLS | 2018/07/30 01:30 | LA Galaxy v Orlando City SC | L | 4-3 |
| USA MLS | 2018/07/27 00:00 | Orlando City SC v New York City FC | L | 0-2 |
| USA MLS | 2018/07/21 23:30 | Columbus Crew v Orlando City SC | L | 3-2 |
| USA US Open Cup | 2018/07/18 23:00 | Philadelphia Union v Orlando City SC | L | 1-0 |
| USA MLS | 2018/07/15 00:00 | Orlando City SC v Toronto FC | W | 2-1 |
Away History
| USA MLS | 2018/08/30 00:00 | DC United v Philadelphia Union | W | 0-2 |
| USA MLS | 2018/08/25 23:00 | Philadelphia Union v New England Revolution | W | 1-0 |
| USA MLS | 2018/08/18 23:00 | Philadelphia Union v New York City FC | W | 2-0 |
| USA MLS | 2018/08/11 23:30 | New England Revolution v Philadelphia Union | W | 2-3 |
| USA US Open Cup | 2018/08/08 23:00 | Philadelphia Union v Chicago Fire | W | 3-0 |
| USA MLS | 2018/08/05 03:00 | Portland Timbers v Philadelphia Union | L | 3-0 |
| USA MLS | 2018/07/26 01:00 | Houston Dynamo v Philadelphia Union | W | 1-3 |
| USA MLS | 2018/07/21 23:00 | Philadelphia Union v LA Galaxy | L | 1-3 |