Stadium: Court 3 Round: 28 Ground: Clay
| 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 |
| 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 Houston MD | 2019/04/11 20:00 | Harrison/McDonald v Krajicek/Sitak | 0-6,5-7 |
| ATP Houston MD | 2019/04/09 00:45 | Hewitt/Thompson v Krajicek/Sitak | 2-6,6-4,8-10 |
| ATP Miami MD | 2019/03/23 19:20 | Bopanna/Shapovalov v Krajicek/Sitak | 7-5,2-6,10-6 |
| Challenger Phoenix MD | 2019/03/17 20:00 | Murray/Skupski v Krajicek/Sitak | 6-7,7-5,10-6 |
| Challenger Phoenix MD | 2019/03/16 21:00 | Cerretani/Monroe v Krajicek/Sitak | 6-4,4-6,7-10 |
| ATP Acapulco MD | 2019/03/03 04:50 | Krajicek/Sitak v Zverev/Zverev | 6-2,6-7,5-10 |
| ATP Acapulco MD | 2019/03/02 01:15 | Granollers/Mektic v Krajicek/Sitak | 3-6,6-3,11-13 |
| ATP Acapulco MD | 2019/02/28 23:00 | Cabal/Farah v Krajicek/Sitak | 6-7,4-6 |