| 2020-10-26 | Vienna | Hard | R32 | 111 |  Kevin Anderson (PR) | 92 |  Dennis Novak (WC) | 6-7(2) 6-4 7-6(6) | H2H | 3 | 164 | 18 | 7 | 61.2% | 84.1% | 50.0% | 0/1 |
| 2020-10-19 | Cologne 2 | Hard | R32 | 141 |  Oscar Otte (LL) | 91 | Dennis Novak (Q) | 6-3 6-2 | H2H | 3 | 63 | 3 | 2 | 62.2% | 75.0% | 64.7% | 2/3 |
| 2020-10-12 | Cologne 1 | Hard | QF | 71 |  Alejandro Davidovich Fokina | 94 | Dennis Novak | 6-3 2-6 6-3 | H2H | 3 | 115 | 0 | 3 | 70.9% | 57.1% | 34.8% | 6/13 |
| 2020-10-12 | Cologne 1 | Hard | R16 | 94 | Dennis Novak | 26 |  Benoit Paire (4) | 6-3 6-4 | H2H | 3 | 64 | 1 | 0 | 68.0% | 73.5% | 68.8% | 2/4 |
| 2020-10-12 | Cologne 1 | Hard | R32 | 94 | Dennis Novak | 59 |  Jordan Thompson | 6-3 6-3 | H2H | 3 | 76 | 1 | 0 | 59.6% | 75.0% | 73.7% | 3/4 |
| 2020-09-28 | Roland Garros | Clay | R128 | 7 | Alexander Zverev (6) | 92 | Dennis Novak | 7-5 6-2 6-4 | H2H | 5 | 125 | 10 | 2 | 72.5% | 82.8% | 59.1% | 1/2 |
| 2020-09-07 | Kitzbuhel | Clay | R32 | 337 | Maximilian Marterer (Q) | 85 | Dennis Novak (WC) | 7-6(6) 6-4 | H2H | 3 | 104 | 4 | 3 | 67.1% | 73.5% | 50.0% | 3/4 |
| 2020-08-31 | US Open | Hard | R128 | 99 | Alejandro Davidovich Fokina | 85 | Dennis Novak | 3-6 6-4 6-3 1-6 6-0 | H2H | 5 | 173 | 2 | 4 | 64.0% | 58.6% | 53.1% | 9/15 |
| 2020-03-06 | Davis Cup QLS R1: AUT vs URU | Hard | RR | 85 | Dennis Novak | 487 |  Martin Cuevas | 6-2 6-4 | H2H | 3 | 78 | 6 | 1 | 69.4% | 76.5% | 73.3% | 1/1 |
| 2020-03-06 | Davis Cup QLS R1: AUT vs URU | Hard | RR | 85 | Dennis Novak | 60 | Pablo Cuevas | 2-6 6-3 6-4 | H2H | 3 | 99 | 5 | 2 | 65.3% | 74.5% | 68.0% | 2/4 |
