Stadium: Italcementi Round: 26 Ground: Hardcourt indoor
| Challenger Orleans MD | 2021/09/29 14:05 | Galloway/Lawson v Glasspool/Heliovaara | 6-3,4-6,12-10 |
| ATP Nur-Sultan MD | 2021/09/24 06:00 | Gonzalez/Molteni v Glasspool/Heliovaara | 5-7,6-4,10-8 |
| ATP Nur-Sultan MD | 2021/09/23 06:00 | Pel/Qureshi v Glasspool/Heliovaara | 6-7,3-6 |
| Wimbledon MD | 2021/07/03 14:00 | Glasspool/Heliovaara v Gray/Mchugh | 4-6,6-3,8-6 |
| Wimbledon MD | 2021/07/01 17:00 | Koolhof/Rojer v Glasspool/Heliovaara | 7-5,3-6,4-6 |
| ATP Eastbourne MD | 2021/06/24 13:45 | Mektic/Pavic v Glasspool/Heliovaara | 6-4,6-7,18-16 |
| ATP Eastbourne MD | 2021/06/23 14:00 | Purcell/Saville v Glasspool/Heliovaara | 2-6,3-6 |
| Challenger Nottingham MD | 2021/06/10 11:35 | Glasspool/Heliovaara v Ebden/Smith | 4-6,2-6 |
| Challenger Trieste MD | 2021/07/28 10:05 | Marfia/Virgili v Added/Sachko | 3-6,2-6 |