Kento Takeuchi defeated Issei Okamura 5-7 6-2 6-2 in the M25 Canberra 3 round of 32 on clay. Kento Takeuchi extended the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2022-03-29 | M25 Canberra 4 | R32 | clay | Issei Okamura | 6-3 4-6 6-4 |
| 2017-07-24 | China F14 | R32 | hard | Issei Okamura | 6-2 6-2 |
| 2017-05-29 | Japan F6 | R32 | clay | Kento Takeuchi | 7-6(8) 6-3 |
| 2016-06-06 | Japan F7 | R32 | hard | Kento Takeuchi | 6-2 6-3 |
| 2016-03-07 | Japan F1 | R32 | hard | Issei Okamura | 7-6(3) 7-6(1) |
| 2015-10-05 | Philippines F1 | QF | clay | Kento Takeuchi | 6-1 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.