| Date | Match | League | Result | OU 2.5 | Both to score |
|---|---|---|---|---|---|
| 8/20/26 | Orlando City vs Chicago Fire | Major League Soccer | 1:2 | Yes | Yes |
| 6/1/25 | Orlando City vs Chicago Fire | Major League Soccer | 1:3 | Yes | Yes |
| 5/4/25 | Chicago Fire vs Orlando City | Major League Soccer | 0:0 | No | No |
| 6/23/24 | Orlando City vs Chicago Fire | Major League Soccer | 4:2 | Yes | Yes |
| 5/30/24 | Chicago Fire vs Orlando City | Major League Soccer | 1:1 | No | Yes |
| 8/21/23 | Chicago Fire vs Orlando City | Major League Soccer | 1:3 | Yes | Yes |
| 7/2/23 | Orlando City vs Chicago Fire | Major League Soccer | 3:1 | Yes | Yes |
| 4/9/22 | Orlando City vs Chicago Fire | Major League Soccer | 1:0 | No | No |
| 3/6/22 | Chicago Fire vs Orlando City | Major League Soccer | 0:0 | No | No |
| 8/22/21 | Orlando City vs Chicago Fire | Major League Soccer | 1:0 | No | No |
| 7/8/21 | Chicago Fire vs Orlando City | Major League Soccer | 3:1 | Yes | Yes |
| 4/3/21 | Orlando City vs Chicago Fire | Club Friendly | 2:2 | Yes | Yes |
| 4/3/21 | Chicago Fire vs Orlando City | Club Friendly | 2:2 | Yes | Yes |
| 9/20/20 | Orlando City vs Chicago Fire | Major League Soccer | 4:1 | Yes | Yes |
| 10/6/19 | Orlando City vs Chicago Fire | Major League Soccer | 2:5 | Yes | Yes |
| 3/9/19 | Chicago Fire vs Orlando City | Major League Soccer | 1:1 | No | Yes |
| 9/16/18 | Chicago Fire vs Orlando City | Major League Soccer | 4:0 | Yes | No |
| 5/27/18 | Orlando City vs Chicago Fire | Major League Soccer | 1:2 | Yes | Yes |
| 5/27/18 | Orlando City vs Chicago Fire | Major League Soccer | 1:2 | Yes | Yes |
| 6/25/17 | Chicago Fire vs Orlando City | Major League Soccer | 4:0 | Yes | No |
| 6/5/17 | Orlando City vs Chicago Fire | Major League Soccer | 0:0 | No | No |