[1] Philadelphia Union 2-0 Chicago Fire [10] 2019-07-20 23:30
Stadium: Subaru Park Round: 1
Referee: Rubiel Vazquez Home Manager: Jim Curtin Away Manager: Veljko Paunovic
Head to Head
| USA US Open Cup | 2018/08/08 23:00 | Philadelphia Union v Chicago Fire | W | 3-0 |
| USA MLS | 2018/07/12 00:30 | Chicago Fire v Philadelphia Union | W | 3-4 |
| USA MLS | 2018/05/30 23:30 | Philadelphia Union v Chicago Fire | W | 3-1 |
| Club Friendly List | 2018/02/08 16:00 | Chicago Fire v Philadelphia Union | D | 0-0 |
| USA MLS | 2017/10/15 21:00 | Chicago Fire v Philadelphia Union | L | 3-2 |
| USA MLS | 2017/09/23 23:00 | Philadelphia Union v Chicago Fire | W | 3-1 |
| Club Friendly List | 2017/02/09 19:00 | Chicago Fire v Philadelphia Union | L | 1-0 |
| USA MLS | 2016/09/04 00:30 | Chicago Fire v Philadelphia Union | L | 3-0 |
| USA MLS | 2016/06/22 23:00 | Philadelphia Union v Chicago Fire | W | 4-3 |
| USA MLS | 2016/04/02 21:00 | Chicago Fire v Philadelphia Union | L | 1-0 |
| Club Friendly List | 2016/02/11 21:00 | Philadelphia Union v Chicago Fire | L | 2-4 |
| USA MLS | 2015/08/16 23:00 | Philadelphia Union v Chicago Fire | D | 3-3 |
| USA US Open Cup | 2015/08/12 23:30 | Philadelphia Union v Chicago Fire | W | 1-0 |
| USA MLS | 2015/03/29 21:00 | Chicago Fire v Philadelphia Union | L | 1-0 |