Stadium: Court 1 Round: 26 Ground: Clay
| ATP Houston MD | 2019/04/14 17:00 | Gonzalez/Qureshi v Skupski/Skupski | 3-6,6-4,10-6 |
| ATP Houston MD | 2019/04/12 21:30 | Skupski/Skupski v Krajicek/Sitak | 6-1,6-4 |
| ATP Houston MD | 2019/04/11 22:25 | Chardy/Martin v Skupski/Skupski | 6-3,3-6,12-14 |
| ATP Houston MD | 2019/04/10 19:50 | Klahn/Querrey v Skupski/Skupski | 3-6,6-2,9-11 |
| 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 |