[3] DC United 1-0 Orlando City SC [9] 2019-06-27 00:00
Stadium: Audi Field Round: 1
Referee: Alex Chilowicz Home Manager: Ben Olsen Away Manager: James O'Connor
Head to Head
| USA MLS | 2019/03/31 22:30 | Orlando City SC v DC United | W | 1-2 |
| USA MLS | 2018/08/13 00:00 | DC United v Orlando City SC | W | 3-2 |
| USA US Open Cup | 2018/06/20 23:00 | DC United v Orlando City SC | L | 3-5 |
| USA MLS | 2018/03/04 00:30 | Orlando City SC v DC United | D | 1-1 |
| USA MLS | 2017/09/09 23:00 | DC United v Orlando City SC | L | 1-2 |
| USA MLS | 2017/05/31 23:30 | Orlando City SC v DC United | L | 2-0 |
| USA MLS | 2016/10/23 20:00 | Orlando City SC v DC United | L | 4-2 |
| USA MLS | 2016/09/24 23:00 | DC United v Orlando City SC | W | 4-1 |
Home History
| USA US Open Cup | 2019/06/19 23:00 | DC United v New York City FC | L | 1-2 |
| USA US Open Cup | 2019/06/12 23:00 | DC United v Philadelphia Union | W | 2-1 |
| USA MLS | 2019/06/02 00:00 | DC United v San Jose Earthquakes | D | 1-1 |
| USA MLS | 2019/05/30 00:00 | DC United v Chicago Fire | D | 3-3 |
| USA MLS | 2019/05/25 23:30 | New England Revolution v DC United | D | 1-1 |
| World Club Friendlies | 2019/05/23 00:00 | DC United v Real Betis | L | 2-5 |
| USA MLS | 2019/05/19 00:30 | Houston Dynamo v DC United | L | 2-1 |
| USA MLS | 2019/05/16 00:00 | Toronto FC v DC United | D | 0-0 |
Away History
| USA US Open Cup | 2019/06/19 23:30 | Orlando City SC v New England Revolution | W | 2-1 |
| USA US Open Cup | 2019/06/13 00:30 | Memphis 901 FC v Orlando City SC | W | 1-3 |
| USA MLS | 2019/06/01 21:00 | CF Montreal v Orlando City SC | W | 0-3 |
| USA MLS | 2019/05/24 23:00 | Orlando City SC v LA Galaxy | L | 0-1 |
| USA MLS | 2019/05/19 19:00 | Orlando City SC v FC Cincinnati | W | 5-1 |
| USA MLS | 2019/05/16 02:30 | Seattle Sounders v Orlando City SC | L | 2-1 |
| USA MLS | 2019/05/12 18:30 | Atlanta United v Orlando City SC | L | 1-0 |
| USA MLS | 2019/05/04 20:00 | Orlando City SC v Toronto FC | L | 0-2 |
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