Stadium: Soldier Field
Referee: Marcos De Oliveira Home Manager: Raphael Wicky Away Manager: Jim Curtin
| USA MLS | 2020/10/28 23:30 | Philadelphia Union v Chicago Fire | L | 2-1 |
| Club Friendly List | 2020/02/01 21:00 | Chicago Fire v Philadelphia Union | L | 0-3 |
| USA MLS | 2019/08/18 00:00 | Chicago Fire v Philadelphia Union | W | 2-0 |
| USA MLS | 2019/07/20 23:30 | Philadelphia Union v Chicago Fire | L | 2-0 |
| USA US Open Cup | 2018/08/08 23:00 | Philadelphia Union v Chicago Fire | L | 3-0 |
| USA MLS | 2018/07/12 00:30 | Chicago Fire v Philadelphia Union | L | 3-4 |
| USA MLS | 2018/05/30 23:30 | Philadelphia Union v Chicago Fire | L | 3-1 |
| Club Friendly List | 2018/02/08 16:00 | Chicago Fire v Philadelphia Union | D | 0-0 |
| USA MLS | 2020/11/08 20:30 | Chicago Fire v New York City FC | L | 3-4 |
| USA MLS | 2020/11/05 01:00 | Minnesota United v Chicago Fire | D | 2-2 |
| USA MLS | 2020/11/01 00:30 | Nashville SC v Chicago Fire | D | 1-1 |
| USA MLS | 2020/10/28 23:30 | Philadelphia Union v Chicago Fire | L | 2-1 |
| USA MLS | 2020/10/24 23:30 | Chicago Fire v New York Red Bulls | D | 2-2 |
| USA MLS | 2020/10/17 19:30 | Chicago Fire v Sporting Kansas City | D | 2-2 |
| USA MLS | 2020/10/11 23:30 | Chicago Fire v DC United | W | 2-1 |
| USA MLS | 2020/10/08 00:30 | Sporting Kansas City v Chicago Fire | L | 1-0 |
| USA MLS Play-Offs | 2020/11/25 01:00 | Philadelphia Union v New England Revolution | L | 0-2 |
| USA MLS | 2020/11/08 20:30 | Philadelphia Union v New England Revolution | W | 2-0 |
| USA MLS | 2020/11/01 20:30 | Columbus Crew v Philadelphia Union | L | 2-1 |
| USA MLS | 2020/10/28 23:30 | Philadelphia Union v Chicago Fire | W | 2-1 |
| USA MLS | 2020/10/24 23:30 | Philadelphia Union v Toronto FC | W | 5-0 |
| USA MLS | 2020/10/19 23:30 | New England Revolution v Philadelphia Union | W | 1-2 |
| USA MLS | 2020/10/15 00:00 | DC United v Philadelphia Union | D | 2-2 |
| USA MLS | 2020/10/11 23:30 | Philadelphia Union v CF Montreal | W | 2-1 |