Stadium: Court 8 Round: 25 Ground: Clay
| ITF Italy F34 | 2018/10/31 12:00 | Bortolotti, Marco v Winkler, Georg | 6-2,6-3 |
| ITF Italy F34 | 2018/10/30 12:50 | Loccisano, Mike v Winkler, Georg | 5-7,3-6 |
| ITF Italy F33 | 2018/10/24 16:15 | Winkler, Georg v Giner, Marc | 5-7,6-2,2-6 |
| ITF Italy F33 | 2018/10/23 13:55 | Lopez San Martin, Alvaro v Winkler, Georg | 6-2,3-6,6-7 |
| ITF Italy F33 | 2018/10/21 12:00 | Mircea-Alexandru Jecan v Winkler, Georg | 3-6,6-3,6-2 |
| ITF Italy F33 | 2018/10/20 11:00 | Donarski, Sid v Winkler, Georg | 1-6,3-6 |
| ITF Italy F31 | 2018/10/08 13:00 | Eremin, Edoardo v Winkler, Georg | 6-3,6-1 |
| ITF Italy F31 | 2018/10/07 08:00 | Winkler, Georg v Nicolas Parizzia | 6-2,6-3 |
| ITF - M15 Antalya | 2019/01/17 09:00 | Fawcett, Tom v Galoppini, Davide | 3-6,2-6 |
| ITF - M15 Antalya | 2019/01/16 13:40 | Fawcett, Tom v Ergeneman, Gokberk | 6-3,6-4 |
| ITF - M15 Bagnoles-de-l'Orne | 2019/01/08 17:30 | Fawcett, Tom v Lescure, Mick | 3-6,4-6 |
| Houston, USA | 2018/11/13 18:10 | Alexis Galarneau v Fawcett, Tom | 6-3,6-2 |
| Challenger Knoxville | 2018/11/04 19:10 | Redlicki, Michael v Fawcett, Tom | 4-6,6-1,6-4 |
| Charlottesville, USA, Qualifying | 2018/10/27 18:00 | Fawcett, Tom v Denis Yevseyev | 1-6,4-6 |
| Challenger Las Vegas | 2018/10/21 18:00 | Jelle Sels v Fawcett, Tom | 6-7,7-6,6-4 |
| Challenger Las Vegas | 2018/10/20 17:00 | Botzer, Bar Tzuf v Fawcett, Tom | 6-7,3-6 |