Stadium: Stadium Round: 29 Ground: Hardcourt outdoor
| ATP Houston MD | 2018/04/12 20:30 | Bryan/Bryan v Skupski/Skupski | 4-6,6-3,10-6 |
| ATP Eastbourne MD | 2017/06/29 14:55 | Bryan/Bryan v Skupski/Skupski | 6-3,6-3 |
| ATP Delray Beach MD | 2019/02/23 17:30 | Bryan/Bryan v Arevalo/Cerretani | 6-3,7-5 |
| ATP Delray Beach MD | 2019/02/21 22:05 | Bryan/Bryan v Mannarino/Nys | 6-3,7-5 |
| ATP Delray Beach MD | 2019/02/21 01:00 | Bryan/Bryan v Krawietz/Mies | 7-6,7-6 |
| ATP New York MD | 2019/02/15 02:20 | Bryan/Bryan v Sandgren/Withrow | 6-7,4-6 |
| Australian Open MD | 2019/01/23 00:00 | Herbert/Mahut v Bryan/Bryan | 6-4,7-6 |
| Australian Open MD | 2019/01/20 03:40 | Carreno-Busta/Lopez v Bryan/Bryan | 3-6,6-7 |
| Australian Open MD | 2019/01/18 05:10 | Mannarino/Mies v Bryan/Bryan | 5-7,6-4,2-6 |
| Australian Open MD | 2019/01/16 04:00 | Bolt/Polmans v Bryan/Bryan | 6-7,6-7 |
| 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 |
| Australian Open MD | 2019/01/17 00:00 | Duckworth/Thompson v Skupski/Skupski | 3-6,4-6 |