01/By surface
each with its own count, at equal weight
Hard
0-1
K. leads 1-0 in 1 meeting on hard
Clay
0-2
K. leads 2-0 in 2 meetings on clay
Grass
0-1
K. leads 1-0 in 1 meeting on grass
02/Every meeting
4 rows, newest first
| Date | Tournament | Surface | Round | Winner | Score, winner first | Ranks, T. first |
|---|---|---|---|---|---|---|
| Apr 28, 2023 | Mutua Madrid OpenMasters 1000 | clay | 2nd round | Khachanov K. | 6-3, 3-6, 6-3 | 97 v 12 |
| Sep 1, 2022 | US OpenGrand Slam, best of 5 | hard | 2nd round | Khachanov K. | 6-3, 6-3, 5-7, 6-4 | 67 v 31 |
| Apr 21, 2022 | Serbia OpenATP250 | clay | quarterfinal | Khachanov K. | 7-5, 6-4 | 110 v 26 |
| Jul 5, 2017 | WimbledonGrand Slam, best of 5 | grass | 2nd round | Khachanov K. | 3-6, 7-6, 7-6, 7-5 | 100 v 34 |
A record, never a share of meetings. Main-draw singles since 2013; a meeting ended by retirement is counted with the sets that were played and marked; a walkover is listed and counted in neither column. Monteiro T. and Khachanov K. each carry the table against every opponent faced.