Stadium: Court 3 Round: 26 Ground: Clay
| ATP Delray Beach MD | 2019/02/24 17:30 | Bryan/Bryan v Skupski/Skupski | 7-6,6-4 |
| ATP Delray Beach MD | 2019/02/24 02:55 | Albot/Nishioka v Skupski/Skupski | 4-6,2-6 |
| ATP Delray Beach MD | 2019/02/20 20:25 | Lorenzi/Seppi v Skupski/Skupski | 6-7,4-6 |
| ATP Delray Beach MD | 2019/02/19 21:25 | Millman/Popyrin v Skupski/Skupski | 2-6,4-6 |
| ATP New York MD | 2019/02/13 20:25 | Krawietz/Mies v Skupski/Skupski | 7-5,7-6 |
| ATP Montpellier MD | 2019/02/07 11:00 | Bonzi/Hoang v Skupski/Skupski | 6-2,7-5 |
| ATP Montpellier MD | 2019/02/05 19:15 | Lindstedt/Puetz v Skupski/Skupski | 3-6,4-6 |
| Australian Open MD | 2019/01/18 03:00 | Kontinen/Peers v Skupski/Skupski | 6-3,6-4 |