| 11 Aug 19 | r50  |  Western and Southern Financial Group Masters De Minaur vs Cecchinato |
| 12 Aug 19 | r50 | Western and Southern Financial Group Masters Isner vs Lajovic |
| 12 Aug 19 | r50 | Western and Southern Financial Group Masters Cilic vs Albot |
| 12 Aug 19 | r50 | Western and Southern Financial Group Masters Garin vs Mannarino |
| 12 Aug 19 | r50 | Western and Southern Financial Group Masters Pouille vs Kudla |
| 12 Aug 19 | r50 | Western and Southern Financial Group Masters Thompson vs Nishioka |
| 12 Aug 19 | r50 | Western and Southern Financial Group Masters Auger Aliassime vs Kecmanovic |
| 12 Aug 19 | r50 | Western and Southern Financial Group Masters Herbert vs Querrey |
| 12 Aug 19 | r50 | Western and Southern Financial Group Masters Pella vs Ruud |
| 12 Aug 19 | r50 | Western and Southern Financial Group Masters Berrettini vs Londero |
| 12 Aug 19 | r50 | Western and Southern Financial Group Masters Gasquet vs Murray |
| 12 Aug 19 | r50 | Western and Southern Financial Group Masters Struff vs Karlovic |
| 12 Aug 19 | r50 | Western and Southern Financial Group Masters Simon vs Carreno Busta |
| 13 Aug 19 | r50 | Western and Southern Financial Group Masters Kyrgios vs Sonego |
| 13 Aug 19 | r50 | Western and Southern Financial Group Masters Wawrinka vs Dimitrov |
| 13 Aug 19 | r50 | Western and Southern Financial Group Masters Goffin vs Fritz |
| 13 Aug 19 | r50 | Western and Southern Financial Group Masters Basilashvili vs Rublev |
| 13 Aug 19 | r50 | Western and Southern Financial Group Masters Paire vs Verdasco |
| 13 Aug 19 | r50 | Western and Southern Financial Group Masters Monfils vs Tiafoe |
| 13 Aug 19 | r50 | Western and Southern Financial Group Masters Schwartzman vs Djere |
| 13 Aug 19 | r50 | Western and Southern Financial Group Masters Shapovalov vs Sousa |
| 13 Aug 19 | r50 | Western and Southern Financial Group Masters Medvedev vs Edmund |
| 13 Aug 19 | r50 | Western and Southern Financial Group Masters Bautista Agut vs Hurkacz |
| 13 Aug 19 | r50 | Western and Southern Financial Group Masters Coric vs Opelka |
| 13 Aug 19 | r50 | Western and Southern Financial Group Masters Djokovic vs Querrey |
| 14 Aug 19 | r50 | Western and Southern Financial Group Masters Federer vs Londero |
| 14 Aug 19 | r50 | Western and Southern Financial Group Masters Isner vs Carreno Busta |
| 14 Aug 19 | r50 | Western and Southern Financial Group Masters De Minaur vs Opelka |
| 14 Aug 19 | r50 | Western and Southern Financial Group Masters Gasquet vs Delbonis |
| 14 Aug 19 | r50 | Western and Southern Financial Group Masters Nishikori vs Nishioka |
| 14 Aug 19 | r50 | Western and Southern Financial Group Masters Medvedev vs Paire |
| 14 Aug 19 | r50 | Western and Southern Financial Group Masters Tsitsipas vs Struff |
| 14 Aug 19 | r50 | Western and Southern Financial Group Masters Schwartzman vs Albot |
| 14 Aug 19 | r50 | Western and Southern Financial Group Masters Wawrinka vs Rublev |
| 14 Aug 19 | r50 | Western and Southern Financial Group Masters Goffin vs Pella |
| 14 Aug 19 | r50 | Western and Southern Financial Group Masters Zverev vs Kecmanovic |
| 14 Aug 19 | r50 | Western and Southern Financial Group Masters Kukushkin vs Mannarino |
| 14 Aug 19 | r50 | Western and Southern Financial Group Masters Pouille vs Shapovalov |
| 15 Aug 19 | r50 | Western and Southern Financial Group Masters Bautista Agut vs Tiafoe |
| 15 Aug 19 | r50 | Western and Southern Financial Group Masters Khachanov vs Kyrgios |
| 15 Aug 19 | r50 | Western and Southern Financial Group Masters De Minaur vs Nishioka |
| 15 Aug 19 | r50 | Western and Southern Financial Group Masters Schwartzman vs Gasquet |
| 15 Aug 19 | r50 | Western and Southern Financial Group Masters Goffin vs Mannarino |
| 15 Aug 19 | r50 | Western and Southern Financial Group Masters Medvedev vs Struff |
| 15 Aug 19 | r50 | Western and Southern Financial Group Masters Bautista Agut vs Kecmanovic |
| 15 Aug 19 | r50 | Western and Southern Financial Group Masters Federer vs Rublev |
| 15 Aug 19 | r50 | Western and Southern Financial Group Masters Khachanov vs Pouille |
| 16 Aug 19 | r50 | Western and Southern Financial Group Masters Djokovic vs Carreno Busta |
| 16 Aug 19 | r50 | Western and Southern Financial Group Masters Bautista Agut vs Gasquet |
| 16 Aug 19 | r50 | Western and Southern Financial Group Masters Goffin vs Nishioka |
| 17 Aug 19 | r50 | Western and Southern Financial Group Masters Medvedev vs Rublev |
| 17 Aug 19 | r50 | Western and Southern Financial Group Masters Djokovic vs Pouille |
| 17 Aug 19 | r50 | Western and Southern Financial Group Masters Goffin vs Gasquet |
| 17 Aug 19 | r50 | Western and Southern Financial Group Masters Djokovic vs Medvedev |
| 18 Aug 19 | r50 | Western and Southern Financial Group Masters Medvedev vs Goffin |
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