Stadium: Centre Court Round: 26 Ground: Hardcourt outdoor
| Challenger Burnie | 2019/01/22 06:30 | James Duckworth v Marc Polmans | 4-6,6-3,4-6 |
| Challenger Burnie | 2019/01/21 04:10 | James Duckworth v Aleksandar Vukic | 6-2,6-3 |
| Australian Open | 2019/01/14 01:30 | James Duckworth v Rafael Nadal | 4-6,3-6,5-7 |
| ATP Sydney | 2019/01/08 05:50 | Marton Fucsovics v James Duckworth | 3-6,6-3,6-4 |
| ATP Brisbane | 2019/01/01 03:15 | James Duckworth v Andy Murray | 3-6,4-6 |
| Australian Open WC | 2018/12/16 02:05 | Luke Saville v James Duckworth | 3-6,7-5,5-7,6-7 |
| Australian Open WC | 2018/12/14 03:00 | James Duckworth v Maverick Banes | 6-7,7-5,6-1,6-3 |
| Australian Open WC | 2018/12/12 01:30 | Rinky Hijikata v James Duckworth | 3-6,4-6,6-3,3-6 |
| Australian Open | 2019/01/14 01:35 | Grigor Dimitrov v Janko Tipsarevic | 4-6,6-3,6-1,6-4 |
| Kooyong Classic | 2019/01/08 02:35 | Jason Kubler v Janko Tipsarevic | 4-6,6-3,10-12 |
| US Open | 2017/08/30 23:05 | Diego Schwartzman v Janko Tipsarevic | 6-2,6-4,7-5 |
| US Open | 2017/08/28 19:35 | Thanasi Kokkinakis v Janko Tipsarevic | 7-6,6-3,1-6,6-7,3-6 |
| ATP Winston-Salem | 2017/08/21 19:00 | Janko Tipsarevic v Andreas Seppi | 2-6,2-6 |
| ATP Cincinnati | 2017/08/16 15:00 | David Ferrer v Janko Tipsarevic | 6-4,6-7,6-1 |
| ATP Cincinnati Qual | 2017/08/13 19:40 | Janko Tipsarevic v Christopher Eubanks | 3-6,4-6 |
| ATP Cincinnati Qual | 2017/08/12 21:25 | Janko Tipsarevic v John McNally | 5-7,6-1,7-6 |