Stadium: Court Philippe Chatrier Round: 26 Ground: Clay
| ATP Cincinnati | 2018/08/17 18:00 | Leonardo Mayer v Roger Federer | 1-6,6-7 |
| US Open | 2015/09/01 18:30 | Leonardo Mayer v Roger Federer | 1-6,2-6,2-6 |
| Challenger Shanghai | 2014/10/08 13:45 | Roger Federer v Leonardo Mayer | 7-5,3-6,7-6 |
| ATP Brisbane | 2018/12/31 07:20 | Leonardo Mayer v Miomir Kecmanovic | 3-6,1-6 |
| ATP Basel | 2018/10/23 19:30 | Leonardo Mayer v Gilles Simon | 3-6,3-6 |
| ATP Antwerp | 2018/10/15 12:40 | Leonardo Mayer v Vasek Pospisil | 3-6,5-7 |
| ATP Shanghai | 2018/10/09 05:00 | Leonardo Mayer v Richard Gasquet | 6-1,2-6,1-6 |
| ATP Beijing | 2018/10/02 04:30 | Matteo Berrettini v Leonardo Mayer | 6-3,6-2 |
| ATP Winston-Salem | 2018/08/21 23:10 | Leonardo Mayer v Kyle Edmund | 3-6,3-6 |
| ATP Winston-Salem | 2018/08/20 19:00 | Leonardo Mayer v Yuichi Sugita | 6-3,7-6 |
| ATP Cincinnati | 2018/08/17 18:00 | Leonardo Mayer v Roger Federer | 1-6,6-7 |
| Hopman Cup | 2019/01/01 09:30 | Frances Tiafoe v Roger Federer | 4-6,1-6 |
| Hopman Cup | 2018/12/30 09:30 | Cameron Norrie v Roger Federer | 1-6,1-6 |
| ATP World Tour Finals | 2018/11/17 14:00 | Roger Federer v Alexander Zverev | 5-7,6-7 |
| ATP World Tour Finals | 2018/11/15 20:00 | Roger Federer v Kevin Anderson | 6-4,6-3 |
| ATP World Tour Finals | 2018/11/13 20:00 | Roger Federer v Dominic Thiem | 6-2,6-3 |
| ATP World Tour Finals | 2018/11/11 20:00 | Roger Federer v Kei Nishikori | 6-7,3-6 |
| ATP Paris | 2018/11/03 15:30 | Roger Federer v Novak Djokovic | 6-7,7-5,6-7 |
| ATP Paris | 2018/11/02 21:05 | Kei Nishikori v Roger Federer | 4-6,4-6 |