Stadium: Court 9 Round: 24 Ground: Hardcourt outdoor
| ATP Cincinnati - MD | 2021/08/19 21:15 | Monroe/Tiafoe v Ram/Salisbury | 6-7,2-6 |
| ATP Cincinnati - MD | 2021/08/16 19:20 | Golubev/Mies v Monroe/Tiafoe | 6-7,5-7 |
| French Open - MD | 2021/06/03 09:00 | Bopanna/Skugor v Monroe/Tiafoe | 6-4,7-5 |
| French Open - MD | 2021/06/01 15:45 | Monroe/Tiafoe v Kubot/Melo | 6-3,6-4 |
| ATP Estoril - MD | 2021/04/29 10:30 | Monroe/Tiafoe v Klaasen/Mclachlan | 3-6,7-6,6-10 |
| ATP Estoril - MD | 2021/04/27 11:40 | Silva/Sousa v Monroe/Tiafoe | 4-6,2-6 |
| ATP Miami - MD | 2021/03/27 17:50 | Monroe/Tiafoe v Evans/Skupski | 6-7,2-6 |
| Australian Open - MD | 2021/02/14 04:20 | Monroe/Tiafoe v Daniell/Oswald | 3-6,5-7 |