Head to Head
| USA MLS | 2016/09/04 00:30 | Chicago Fire v Philadelphia Union | W | 3-0 |
| USA MLS | 2016/06/22 23:00 | Philadelphia Union v Chicago Fire | L | 4-3 |
| USA MLS | 2016/04/02 21:00 | Chicago Fire v Philadelphia Union | W | 1-0 |
| Club Friendly List | 2016/02/11 21:00 | Philadelphia Union v Chicago Fire | W | 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 | L | 1-0 |
| USA MLS | 2015/03/29 21:00 | Chicago Fire v Philadelphia Union | W | 1-0 |
Home History
| USA MLS | 2016/10/23 20:00 | Toronto FC v Chicago Fire | L | 3-2 |
| USA MLS | 2016/10/16 19:00 | Chicago Fire v New England Revolution | W | 2-1 |
| USA MLS | 2016/10/14 00:30 | Chicago Fire v Columbus Crew | D | 2-2 |
| USA MLS | 2016/10/01 23:30 | Columbus Crew v Chicago Fire | L | 3-0 |
| USA MLS | 2016/09/29 02:30 | Seattle Sounders v Chicago Fire | L | 1-0 |
| USA MLS | 2016/09/24 00:00 | New York City FC v Chicago Fire | L | 4-1 |
| USA MLS | 2016/09/17 00:00 | Chicago Fire v DC United | D | 2-2 |
| USA MLS | 2016/09/11 00:30 | Chicago Fire v Toronto FC | L | 1-2 |
Away History
| USA MLS Play-Offs | 2016/10/26 23:30 | Toronto FC v Philadelphia Union | L | 3-1 |
| USA MLS | 2016/10/23 20:00 | Philadelphia Union v New York Red Bulls | L | 0-2 |
| USA MLS | 2016/10/16 19:00 | Philadelphia Union v Orlando City SC | L | 0-2 |
| USA MLS | 2016/10/01 23:00 | New York Red Bulls v Philadelphia Union | L | 3-2 |
| USA MLS | 2016/09/24 21:00 | Toronto FC v Philadelphia Union | D | 1-1 |
| USA MLS | 2016/09/17 22:00 | Portland Timbers v Philadelphia Union | L | 2-1 |
| USA MLS | 2016/09/10 23:00 | Philadelphia Union v CF Montreal | D | 1-1 |
| USA MLS | 2016/09/04 00:30 | Chicago Fire v Philadelphia Union | L | 3-0 |