Stadium: Court 14 Round: 25 Ground: Grass
| Wimbledon MD | 2021/07/01 17:00 | Koolhof W / Rojer J-J 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 | 푸르셀 M / 사빌 L 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 Nottingham MD | 2021/06/09 10:00 | Glasspool/Heliovaara v Gray/Parker | 6-2,6-3 |
| Challenger Rome MD | 2021/04/22 10:45 | Galloway R / Lawson A v Glasspool/Heliovaara | 6-7,6-3,10-8 |
| Challenger Belgrade MD | 2021/04/14 13:35 | Glasspool/Heliovaara v Sitak/Vega Hernandez | 6-2,4-6,5-10 |
| ATP Marseille MD | 2021/03/14 10:45 | Glasspool/Heliovaara v 아렌드 A / 펠 D | 7-5,7-6 |
| Wimbledon MD | 2021/07/02 11:15 | 제바비 R / 베슬리 J v Gray/Mchugh | 6-7,3-6 |