[4] Orlando City SC 2-1 Philadelphia Union [2] 2021-05-19 20:25
Stadium: Inter&Co Stadium
Referee: Alan Kelly Home Manager: Oscar Pareja Away Manager: Jim Curtin
Head to Head
| USA MLS is Back Tournament | 2020/07/21 00:00 | Philadelphia Union v Orlando City SC | D | 1-1 |
| USA MLS | 2019/07/07 20:30 | Philadelphia Union v Orlando City SC | D | 2-2 |
| USA MLS | 2019/07/03 23:30 | Orlando City SC v Philadelphia Union | L | 1-3 |
| USA MLS | 2018/09/01 23:30 | Orlando City SC v Philadelphia Union | D | 2-2 |
| 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 |
Home History
| USA MLS | 2021/05/17 00:00 | DC United v Orlando City SC | W | 0-1 |
| USA MLS | 2021/05/08 22:00 | Orlando City SC v New York City FC | D | 1-1 |
| USA MLS | 2021/05/01 23:30 | Orlando City SC v FC Cincinnati | W | 3-0 |
| USA MLS | 2021/04/23 23:30 | Sporting Kansas City v Orlando City SC | D | 1-1 |
| USA MLS | 2021/04/17 19:00 | Orlando City SC v Atlanta United | D | 0-0 |
| USA MLS Play-Offs | 2020/11/29 20:00 | Orlando City SC v New England Revolution | L | 1-3 |
| USA MLS Play-Offs | 2020/11/21 17:00 | Orlando City SC v New York City FC | W | 7-6 |
| USA MLS | 2020/11/08 20:30 | Orlando City SC v Nashville SC | L | 2-3 |
Away History
| USA MLS | 2021/05/15 23:30 | Philadelphia Union v New York Red Bulls | W | 1-0 |
| USA MLS | 2021/05/12 23:30 | Philadelphia Union v New England Revolution | D | 1-1 |
| USA MLS | 2021/05/08 17:00 | Chicago Fire v Philadelphia Union | W | 0-2 |
| CONCACAF Champions Cup | 2021/05/05 00:00 | Philadelphia Union v Atlanta United | D | 1-1 |
| USA MLS | 2021/05/01 23:30 | Philadelphia Union v New York City FC | L | 0-2 |
| CONCACAF Champions Cup | 2021/04/28 00:00 | Atlanta United v Philadelphia Union | W | 0-3 |
| USA MLS | 2021/04/25 00:00 | Philadelphia Union v Inter Miami CF | L | 1-2 |
| USA MLS | 2021/04/18 21:30 | Columbus Crew v Philadelphia Union | D | 0-0 |