Stadium: Court 4 Round: 24 Ground: Hardcourt outdoor
| Challenger Bendigo | 2020/01/14 00:35 | Marcos Giron v Pervolarakis, Michail | 6-3,6-0 |
| Challenger Bendigo | 2020/01/12 23:00 | Pervolarakis, Michail v Granollers, Gerard | 7-6,6-3 |
| ATP Cup, Playoffs | 2020/01/07 07:30 | Pervolarakis, Michail v John Millman | 6-4,1-6,6-7 |
| ATP Cup, Playoffs | 2020/01/05 07:30 | Jan-Lennard Struff v Pervolarakis, Michail | 6-4,6-1 |
| ATP Cup, Playoffs | 2020/01/03 00:00 | Pervolarakis, Michail v Felix Auger Aliassime | 1-6,3-6 |
| ITF - M15 Héraklion | 2019/12/12 10:55 | Pervolarakis, Michail v Smirnov, Artem | 3-6,6-2,5-7 |
| ITF - M15 Héraklion | 2019/12/11 08:00 | Pervolarakis, Michail v Kalovelonis, Markos | 6-3,3-6,6-3 |
| ITF - M15 Héraklion | 2019/12/05 08:00 | Pervolarakis, Michail v Alibek Kachmazov | 4-6,4-6 |
| ITF M25 Rancho Santa Fe | 2020/01/16 19:50 | Simon, Tobias v Emilio Nava | 6-7,6-7 |
| ITF M25 Rancho Santa Fe | 2020/01/15 22:25 | Bangoura, Sekou v Simon, Tobias | 3-6,2-6 |
| ITF M25 Rancho Santa Fe | 2020/01/14 20:00 | Simon, Tobias v Gomez, Lucas | 2-6,6-1,10-1 |
| ITF M25 Rancho Santa Fe | 2020/01/13 18:00 | Simon, Tobias v Kyle Kang | 6-3,6-3 |
| Ann Arbor, USA | 2020/01/08 18:10 | Simon, Tobias v Quiroz, Roberto | 4-6,7-6,6-7 |
| Ann Arbor, USA | 2020/01/06 22:25 | Simon, Tobias v King, Evan | 6-4,6-2 |
| ITF - M15 Héraklion | 2019/11/27 11:30 | Boris Pokotilov v Simon, Tobias | 6-4,6-4 |
| Sarreguemines, Singles M-ITF-FRA-22A | 2019/11/24 14:00 | Simon, Tobias v Antoine Bellier | 4-6,6-7 |