| Wimbledon MD | 06/29 16:55 | 24 | Glasspool/Heliovaara v Gaston/Musetti | 6-3,6-3,6-4 | |
| ATP Eastbourne MD | 06/22 13:15 | 27 | 무라이 J / 소아레스 B v Glasspool/Heliovaara | 6-4,7-5 | |
| ATP Eastbourne MD | 06/21 14:15 | 26 | Goransson/Mclachlan v Glasspool/Heliovaara | 6-7,7-6,4-10 | |
| ATP Queens MD | 06/19 14:50 | 29 | Glasspool/Heliovara v Mektic/Pavic | 6-3,6-7,6-10 | |
| ATP Queens MD | 06/18 16:30 | 28 | Glasspool/Heliovara v 보판나 R / 사포발로브 D | 7-5,6-7,10-4 | |
| ATP Queens MD | 06/16 15:20 | 27 | 람 R / 살리스부리 J v Glasspool/Heliovara | 6-7,2-6 | |
| ATP Queens MD | 06/14 18:10 | 26 | 마후트 N / 로젤 - 바셀린 E v Glasspool/Heliovara | 5-7,3-6 | |
| French Open MD | 05/30 16:45 | 27 | Glasspool/Heliovaara v Bopanna/Middelkoop | 6-4,4-6,6-7 | |
| French Open MD | 05/28 10:30 | 26 | Nys/Zielinski v Glasspool/Heliovaara | 6-7,3-6 | |
| French Open MD | 05/27 10:55 | 25 | 베할 A / 에스코발 G v Glasspool/Heliovaara | 4-6,2-6 | |
| French Open MD | 05/25 15:00 | 24 | Glasspool/Heliovaara v 크라위에츠 K / 미에스 A | 6-4,6-2 | |
| ATP Geneva MD | 05/16 14:00 | 26 | Andujar/Middelkoop v Glasspool/Heliovaara | Cancelled | |
| ATP Rome MD | 05/13 12:40 | 27 | Glasspool/Heliovaara v Isner/Schwartzman | 3-6,2-6 | |
| ATP Rome MD | 05/12 12:05 | 26 | Glasspool/Heliovaara v Kokkinakis/Tiafoe | 6-3,3-6,10-8 | |
| ATP Rome MD | 05/11 13:50 | 25 | 람 R / 살리스부리 J v Glasspool/Heliovaara | 6-7,3-6 | |
| Challenger Aix en Provence MD | 05/05 08:30 | 27 | Wayenburg/Van Assche v Glasspool/Heliovaara | 6-4,3-6,11-9 | |
| Challenger Aix en Provence MD | 05/04 10:45 | 26 | Arneodo/Walkow v Glasspool/Heliovaara | 4-6,7-6,4-10 | |
| ATP Munich MD | 04/30 09:30 | 28 | 크라위에츠 K / 미에스 A v Glasspool/Heliovaara | 7-5,6-3 | |
| ATP Munich MD | 04/28 12:15 | 27 | Glasspool/Heliovaara v Peers/Polasek | 7-6,7-6 | |
| ATP Munich MD | 04/27 14:05 | 26 | Cornea/Tsitsipas v Glasspool/Heliovaara | 4-6,1-6 | |
| ATP Belgrade MD | 04/18 15:00 | 26 | Glasspool/Heliovaara v 베할 A / 에스코발 G | 4-6,3-6 | |
| ATP Marrakech MD | 04/06 17:00 | 26 | Cecchinato/Musetti v Glasspool/Heliovaara | 6-4,1-6,10-7 | |
| ATP Marrakech MD | 04/06 14:25 | 26 | 에반스 D / 스쿠프스키 K v Glasspool/Heliovaara | Cancelled | |
| ATP Acapulco MD | 02/26 04:00 | 28 | Glasspool/Heliovaara v Lopez/Tsitsipas | 4-6,4-6 | |
| ATP Acapulco MD | 02/25 01:00 | 27 | Glasspool/Heliovaara v 무라이 J / 소아레스 B | 4-6,6-3,10-6 | |
| ATP Acapulco MD | 02/23 03:35 | 26 | Melo M / Zverev A v Glasspool/Heliovaara | 2-6,6-4,6-10 | |
| ATP Acapulco MD | 02/21 03:05 | 19 | 사빌 L / 스미스 J-P v Glasspool/Heliovaara | 6-4,4-6,10-4 | |
| ATP Acapulco MD | 02/20 04:00 | 14 | 레예스-바렐라 M / 슈누르 M v Glasspool/Heliovaara | 3-6,4-6 | |
| ATP Delray Beach MD | 02/16 16:00 | 26 | Glasspool/Heliovaara v Krajicek/Nys | 6-7,5-7 | |
| ATP Dallas MD | 02/13 21:10 | 29 | Arevalo/Rojer v Glasspool/Heliovaara | 7-6,6-4 |