Stadium: Inter&Co Stadium Round: 1
Referee: David Gantar Home Manager: James O'Connor Away Manager: Caleb Porter
| USA MLS | 2018/10/21 19:00 | Orlando City SC v Columbus Crew | W | 2-1 |
| USA MLS | 2018/07/21 23:30 | Columbus Crew v Orlando City SC | L | 3-2 |
| USA MLS | 2017/10/15 21:00 | Orlando City SC v Columbus Crew | L | 0-1 |
| USA MLS | 2017/08/19 23:30 | Orlando City SC v Columbus Crew | D | 1-1 |
| USA MLS | 2017/04/01 20:00 | Columbus Crew v Orlando City SC | L | 2-0 |
| USA MLS | 2016/09/17 23:30 | Orlando City SC v Columbus Crew | L | 1-4 |
| USA MLS | 2016/07/23 23:30 | Columbus Crew v Orlando City SC | D | 2-2 |
| USA MLS | 2015/08/01 23:30 | Orlando City SC v Columbus Crew | W | 5-2 |
| USA MLS | 2019/03/02 19:30 | Orlando City SC v New York City FC | D | 2-2 |
| World Club Friendlies | 2019/02/21 00:30 | Orlando City SC v New England Revolution | W | 6-2 |
| World Club Friendlies | 2019/02/17 00:30 | Orlando City SC v New York City FC | W | 2-1 |
| USA MLS | 2018/10/28 20:30 | New York Red Bulls v Orlando City SC | L | 1-0 |
| USA MLS | 2018/10/21 19:00 | Orlando City SC v Columbus Crew | W | 2-1 |
| USA MLS | 2018/10/17 23:30 | Orlando City SC v Seattle Sounders | L | 1-2 |
| USA MLS | 2018/10/13 23:30 | New England Revolution v Orlando City SC | L | 2-0 |
| USA MLS | 2018/10/07 00:00 | FC Dallas v Orlando City SC | L | 2-0 |
| USA MLS | 2019/03/02 21:30 | Columbus Crew v New York Red Bulls | D | 1-1 |
| World Club Friendlies | 2019/02/23 22:00 | FC Cincinnati v Columbus Crew | W | 0-3 |
| World Club Friendlies | 2019/02/20 22:00 | Charleston Battery v Columbus Crew | D | 1-1 |
| World Club Friendlies | 2019/02/16 22:00 | Columbus Crew v Chicago Fire | D | 1-1 |
| Club Friendly List | 2019/02/04 22:00 | Los Angeles FC v Columbus Crew | W | 2-4 |
| World Club Friendlies | 2019/01/29 03:00 | Columbus Crew v Vissel Kobe | D | 0-0 |
| USA MLS Play-Offs | 2018/11/12 00:30 | New York Red Bulls v Columbus Crew | L | 3-0 |
| USA MLS Play-Offs | 2018/11/04 20:00 | Columbus Crew v New York Red Bulls | W | 1-0 |