| Challenger Parma 2 | 11/03 09:30 | 25 | [123] Jeffrey John Wolf v Blaz Kavcic [268] | Retired | |
| Challenger Hamburg | 10/29 13:00 | 26 | [123] Jeffrey John Wolf v Roman Safiullin [184] | 6-7,4-6 | |
| Challenger Hamburg | 10/27 10:00 | 25 | [123] Jeffrey John Wolf v Matthias Bachinger [280] | 6-4,6-3 | |
| Challenger Hamburg | 10/27 09:00 | 25 | Jeffrey John Wolf v Martin Klizan | View | |
| ATP Kolín nad Rýnem 2 | 10/17 11:15 | 64 | [123] Jeffrey John Wolf v Alexei Popyrin [108] | 3-6,6-4,3-6 | |
| ATP Petrohrad | 10/13 12:00 | 25 | [123] Jeffrey John Wolf v Milos Raonic [21] | 6-7,1-6 | |
| ATP Petrohrad | 10/11 12:35 | 164 | [120] Jeffrey John Wolf v Alen Avidzba [470] | 3-6,7-5,6-1 | |
| ATP Petrohrad | 10/10 11:00 | 64 | [120] Jeffrey John Wolf v Alexey Vatutin [235] | 4-6,6-1,6-3 | |
| French Open | 09/21 13:25 | 14 | [120] Jeffrey John Wolf v Roberto Marcora [170] | 4-6,3-6 | |
| US Open | 09/05 16:00 | 25 | [138] Jeffrey John Wolf v Daniil Medvedev [5] | 3-6,3-6,2-6 | |
| US Open | 09/03 18:00 | 24 | [138] Jeffrey John Wolf v Roberto Carballes Baena [101] | 6-2,6-4,6-3 | |
| US Open | 09/01 19:55 | 23 | [36] Guido Pella v Jeffrey John Wolf [138] | 2-6,6-0,3-6,3-6 |