Stadium: Court 7 Round: 25 Ground: Hardcourt outdoor
| Australian Open MD | 2021/02/11 04:25 | Granollers/Zeballos v Monroe/Tiafoe | 5-7,4-6 |
| ATP Murray River Open MD | 2021/02/05 08:15 | Melo/Tecau v Monroe/Tiafoe | 7-6,6-2 |
| ATP Murray River Open MD | 2021/02/02 09:50 | Kyrgios/Reid v Monroe/Tiafoe | 5-7,4-6 |
| ATP Delray Beach MD | 2021/01/10 22:05 | Monroe/Tiafoe v McDonald/Paul | 3-6,1-6 |
| ATP Delray Beach MD | 2021/01/07 16:00 | Bambridge/Inglot v Monroe/Tiafoe | 6-3,3-6,4-10 |
| ATP Atlanta MD | 2019/07/24 17:15 | Arevalo/Reyes-Varela v Monroe/Tiafoe | 6-3,6-4 |
| Australian Open MD | 2021/02/11 03:50 | Pospisil/Shapovalov v Martin/Weissborn | 6-3,7-6 |
| Davis Cup | 2019/11/23 13:40 | Khachanov/Rublev v Pospisil/Shapovalov | 3-6,6-3,6-7 |
| Davis Cup | 2019/11/21 21:25 | Peers/Thompson v Pospisil/Shapovalov | 4-6,4-6 |
| Davis Cup | 2019/11/18 21:15 | Berrettini/Fognini v Pospisil/Shapovalov | 6-2,3-6,6-3 |