Stadium: Yankee Stadium Round: 1
Referee: Alex Chilowicz Home Manager: Domenec Torrent Away Manager: Jim Curtin
| USA MLS Play-Offs | 2018/10/31 23:00 | New York City FC v Philadelphia Union | W | 3-1 |
| USA MLS | 2018/10/28 20:30 | New York City FC v Philadelphia Union | W | 3-1 |
| USA MLS | 2018/08/18 23:00 | Philadelphia Union v New York City FC | L | 2-0 |
| USA MLS | 2017/06/03 17:00 | New York City FC v Philadelphia Union | W | 2-1 |
| USA MLS | 2017/04/14 23:00 | Philadelphia Union v New York City FC | W | 0-2 |
| USA MLS | 2016/06/18 17:00 | New York City FC v Philadelphia Union | W | 3-2 |
| USA MLS | 2016/04/23 20:00 | Philadelphia Union v New York City FC | L | 2-0 |
| USA MLS | 2015/06/06 23:00 | Philadelphia Union v New York City FC | W | 1-2 |
| USA MLS | 2019/05/25 19:30 | Chicago Fire v New York City FC | D | 1-1 |
| USA MLS | 2019/05/11 20:00 | LA Galaxy v New York City FC | W | 0-2 |
| USA MLS | 2019/05/04 21:00 | CF Montreal v New York City FC | W | 0-2 |
| USA MLS | 2019/04/27 17:00 | New York City FC v Orlando City SC | D | 1-1 |
| USA MLS | 2019/04/24 23:00 | New York City FC v Chicago Fire | W | 1-0 |
| USA MLS | 2019/04/21 20:00 | DC United v New York City FC | W | 0-2 |
| USA MLS | 2019/04/13 21:00 | Minnesota United v New York City FC | D | 3-3 |
| USA MLS | 2019/04/06 17:00 | New York City FC v CF Montreal | D | 0-0 |
| USA MLS | 2019/05/30 00:25 | Philadelphia Union v Colorado Rapids | D | 1-1 |
| USA MLS | 2019/05/25 23:30 | Philadelphia Union v Portland Timbers | L | 1-3 |
| USA MLS | 2019/05/18 23:30 | Philadelphia Union v Seattle Sounders | D | 0-0 |
| USA MLS | 2019/05/11 19:00 | Toronto FC v Philadelphia Union | W | 1-2 |
| USA MLS | 2019/05/04 23:30 | Philadelphia Union v New England Revolution | W | 6-1 |
| USA MLS | 2019/05/01 23:30 | Philadelphia Union v FC Cincinnati | W | 2-0 |
| USA MLS | 2019/04/27 21:00 | Vancouver Whitecaps v Philadelphia Union | D | 1-1 |
| USA MLS | 2019/04/20 17:00 | Philadelphia Union v CF Montreal | W | 3-0 |