Cannon Kingsley leads 3 to 2 over 5 singles meetings since 2021. Last meeting on 24/04/2026 at M15 Orlando.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 24/04/2026 | M15 Orlando | Quarter-final | clay | Kingsley | 7-5 2-6 6-3 |
| 27/01/2026 | San Diego Challenger | Qualifiers | hard | Corwin | 6-4 6-4 |
| 22/02/2025 | M15 Naples | Semi-final | clay | Corwin | 7-6(3) 6-1 |
| 06/11/2021 | M15 Ithaca | Semi-final | indoor hard | Kingsley | 6-3 6-2 |
| 22/07/2021 | M15 Edwardsville | Round 2 | hard | Kingsley | 6-2 6-2 |
| clay | Corwin 1 - 1 Kingsley |
| hard | Corwin 1 - 1 Kingsley |
| indoor hard | Corwin 0 - 1 Kingsley |
| 2026 | Corwin 1 - 1 Kingsley |
| 2025 | Corwin 1 - 0 Kingsley |
| 2021 | Corwin 0 - 2 Kingsley |
154 wins, 117 losses since 2021 (56.8%).
Last matches: D V V D V
133 wins, 93 losses since 2021 (58.8%).
Last matches: D V V V V
Cannon Kingsley leads 3 to 2 over 5 singles meetings since 2021.
On 24/04/2026, at M15 Orlando (Quarter-final): Cannon Kingsley won 7-5 2-6 6-3.