Head to Head includes singles and doubles results.
| 09/16/18 | Buddy Koehler over Benjamin Kleinman | 6-3; 6-1 | |
| 09/10/18 | Buddy Koehler over Benjamin Kleinman | 6-1; 6-4 | |
| 07/29/18 | Benjamin Kleinman over Buddy Koehler | 7-5; 6-2 | |
| 07/11/18 | Buddy Koehler over Benjamin Kleinman |
6-3; 3-6; TB 7-4 |
|
| 07/02/18 | Buddy Koehler over Benjamin Kleinman |
7-6; 3-6; TB 7-2 |
|
| 06/03/18 | Benjamin Kleinman ties Buddy Koehler | 7-7 Tie | |
| 04/29/18 | Buddy Koehler over Benjamin Kleinman | 6-0; 6-2 | |
| 09/16/17 | Buddy Koehler over Benjamin Kleinman | 6-4; 6-4 |
