Stadium: Court 4 Round: 24 Ground: Grass
| ATP Eastbourne MD | 2021/06/23 17:15 | Skupski/Skupski v Nys/O'Mara | 6-2,3-6,8-10 |
| ATP Queens MD | 2021/06/16 12:25 | Opelka/Peers v Skupski/Skupski | 6-7,7-6,10-2 |
| French Open MD | 2021/06/01 13:55 | Skupski/Skupski v Cabal/Farah | 4-6,4-6 |
| ATP Lyon MD | 2021/05/18 12:00 | Skupski/Skupski v Nedovyesov/Vavassori | 6-7,3-6 |
| ATP Acapulco MD | 2021/03/21 01:00 | Granollers/Zeballos v Skupski/Skupski | 6-7,4-6 |
| ATP Acapulco MD | 2021/03/20 00:00 | Ram/Salisbury v Skupski/Skupski | 4-6,6-7 |
| ATP Acapulco MD | 2021/03/19 01:15 | Skupski/Skupski v Murray/Soares | 6-3,3-6,12-10 |
| ATP Acapulco MD | 2021/03/17 04:20 | Schwartzman/Sousa v Skupski/Skupski | 4-6,6-7 |
| ATP Queens MD | 2021/06/16 12:00 | Broady/Peniston v Herbert/Mahut | 7-6,2-6,10-12 |
| ATP Queens MD | 2021/06/15 15:00 | Broady/Peniston v Bublik/Monroe | 7-5,6-3 |
| Challenger Nottingham MD | 2021/06/08 17:55 | Broady/Peniston v Polmans/Sitak | 2-6,6-7 |