Stadium: Court 1 Round: 27 Ground: Hardcourt outdoor
| ATP Delray Beach MD | 2019/02/18 21:30 | Smith/Thompson v Lorenzi/Seppi | 2-6,6-3,6-10 |
| 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 |
| Australian Open MD | 2019/01/17 00:00 | Duckworth/Thompson v Skupski/Skupski | 3-6,4-6 |
| ATP Sydney MD | 2019/01/11 02:00 | Skupski/Skupski v Murray/Soares | 6-7,7-5,7-10 |
| ATP Sydney MD | 2019/01/09 04:05 | Bolt/Reid v Skupski/Skupski | 4-6,6-7 |