Stadium: Court 1 Round: 27 Ground: Hardcourt indoor
| ATP Marseille MD | 2021/03/09 16:40 | Skupski/Skupski v McDonald/Nishioka | 6-3,6-3 |
| Australian Open MD | 2021/02/13 04:15 | Skupski/Skupski v Millman/Monteiro | 6-3,6-7,4-6 |
| Australian Open MD | 2021/02/11 01:25 | Skupski/Skupski v Auger Aliassime/Hurkacz | 6-3,6-2 |
| ATP Murray River Open MD | 2021/02/02 23:30 | Behar/Escobar v Skupski/Skupski | 7-6,4-6,10-7 |
| ATP Doha MD | 2020/01/08 12:30 | Skupski/Skupski v Kontinen/Skugor | 7-6,4-6,11-13 |
| ATP Doha MD | 2020/01/07 16:40 | Bedene/Djere v Skupski/Skupski | 7-6,4-6,5-10 |
| ATP Eastbourne MD | 2019/06/25 12:00 | Skupski/Skupski v Daniell/Koolhof | 5-7,6-7 |
| French Open MD | 2019/05/30 11:00 | Bryan/Bryan v Skupski/Skupski | 7-5,7-6 |
| ATP Marseille MD | 2021/03/10 15:30 | Tsitsipas/Tsitsipas v Glasspool/Heliovaara | 5-7,1-6 |
| Challenger Gran Canaria MD | 2021/03/04 15:55 | Glasspool/Heliovaara v Couacaud/Guinard | 6-3,6-7,10-12 |
| Challenger Gran Canaria MD | 2021/03/02 13:55 | Glasspool/Heliovaara v Kavcic/Oliveira | 6-3,7-6 |
| Challenger Gran Canaria MD | 2021/02/27 17:15 | Coppejans/Martos Gornes v Glasspool/Heliovaara | 5-7,1-6 |
| Challenger Gran Canaria MD | 2021/02/26 15:50 | Giustino/Trungelliti v Glasspool/Heliovaara | 0-6,1-6 |
| Challenger Gran Canaria MD | 2021/02/25 17:00 | Esteve Lobato/Garcia-Lopez v Glasspool/Heliovaara | 4-6,1-6 |
| Challenger Gran Canaria MD | 2021/02/23 15:20 | Marrero Curbelo/Nava v Glasspool/Heliovaara | 5-7,1-6 |
| Challenger Biella MD | 2021/02/20 14:45 | Nys/Puetz v Glasspool/Heliovaara | 7-6,6-3 |