| ATP Washington | 08/06 00:15 | 27 | [8] Andrey Rublev v Jeffrey John Wolf [99] | 6-2,6-3 | |
| ATP Washington | 08/05 16:00 | 26 | [28] Holger N Rune v Jeffrey John Wolf [99] | 5-7,6-4,3-6 | |
| ATP Washington | 08/03 20:25 | 25 | [99] Jeffrey John Wolf v Denis Shapovalov [22] | 6-2,6-7,6-3 | |
| ATP Washington | 08/01 18:45 | 24 | [99] Jeffrey John Wolf v Taro Daniel [94] | 6-2,6-3 | |
| ATP Atlanta | 07/23 19:20 | 26 | Donald Young v Jeffrey John Wolf | Retired | |
| Challenger Indianapolis | 07/19 15:25 | 25 | [105] Jeffrey John Wolf v Billy Harris [322] | 4-6,7-6,6-7 | |
| Challenger Indianapolis | 07/18 21:30 | 25 | Jeffrey John Wolf v Andrew Harris | CANC | |
| Challenger Rome GA | 07/15 15:00 | 27 | [329] Yibing Wu v Jeffrey John Wolf [111] | 6-4,6-1 | |
| Challenger Rome GA | 07/13 15:20 | 26 | [360] Shintaro Mochizuki v Jeffrey John Wolf [111] | 3-6,6-7 | |
| Challenger Rome GA | 07/12 15:30 | 25 | [374] Juncheng Shang v Jeffrey John Wolf [111] | 1-6,2-6 | |
| Challenger Orlando | 06/11 15:00 | 28 | [133] Jeffrey John Wolf v Jason Kubler [119] | 1-6,3-6 | |
| Challenger Orlando | 06/10 15:00 | 27 | [133] Jeffrey John Wolf v Tung-Lin Wu [214] | 4-6,6-3,6-2 |