| 15 Aug 16 | r50  |  Western and Southern Financial Group Masters Paire vs Coric |
| 15 Aug 16 | r50 | Western and Southern Financial Group Masters Ferrer vs Benneteau |
| 15 Aug 16 | r50 | Western and Southern Financial Group Masters Almagro vs Donaldson |
| 15 Aug 16 | r50 | Western and Southern Financial Group Masters Anderson vs Dolgopolov |
| 15 Aug 16 | r50 | Western and Southern Financial Group Masters Cuevas vs Querrey |
| 15 Aug 16 | r50 | Western and Southern Financial Group Masters Chardy vs Opelka |
| 15 Aug 16 | r50 | Western and Southern Financial Group Masters Cilic vs Troicki |
| 16 Aug 16 | r50 | Western and Southern Financial Group Masters Simon vs Dimitrov |
| 16 Aug 16 | r50 | Western and Southern Financial Group Masters Kyrgios vs Pouille |
| 16 Aug 16 | r50 | Western and Southern Financial Group Masters Fritz vs Youzhny |
| 16 Aug 16 | r50 | Western and Southern Financial Group Masters Goffin vs Basilashvili |
| 16 Aug 16 | r50 | Western and Southern Financial Group Masters Gasquet vs Mannarino |
| 16 Aug 16 | r50 | Western and Southern Financial Group Masters Jaziri vs Millman |
| 16 Aug 16 | r50 | Western and Southern Financial Group Masters Tomic vs Sousa |
| 16 Aug 16 | r50 | Western and Southern Financial Group Masters Monfils vs Carreno Busta |
| 16 Aug 16 | r50 | Western and Southern Financial Group Masters Johnson vs Delbonis |
| 16 Aug 16 | r50 | Western and Southern Financial Group Masters Baghdatis vs Pospisil |
| 16 Aug 16 | r50 | Western and Southern Financial Group Masters Lopez vs Zverev |
| 16 Aug 16 | r50 | Western and Southern Financial Group Masters Isner vs Fognini |
| 16 Aug 16 | r50 | Western and Southern Financial Group Masters Ramos Vinolas vs Verdasco |
| 17 Aug 16 | r50 | Western and Southern Financial Group Masters Bautista Agut vs Mahut |
| 17 Aug 16 | r50 | Western and Southern Financial Group Masters Zverev vs Sugita |
| 17 Aug 16 | r50 | Western and Southern Financial Group Masters Granollers vs Vesely |
| 17 Aug 16 | r50 | Western and Southern Financial Group Masters Karlovic vs Monaco |
| 17 Aug 16 | r50 | Western and Southern Financial Group Masters Nishikori vs Youzhny |
| 17 Aug 16 | r50 | Western and Southern Financial Group Masters Thiem vs Millman |
| 17 Aug 16 | r50 | Western and Southern Financial Group Masters Wawrinka vs Donaldson |
| 17 Aug 16 | r50 | Western and Southern Financial Group Masters Tsonga vs Opelka |
| 17 Aug 16 | r50 | Western and Southern Financial Group Masters Raonic vs Isner |
| 17 Aug 16 | r50 | Western and Southern Financial Group Masters Monfils vs Baghdatis |
| 17 Aug 16 | r50 | Western and Southern Financial Group Masters Lopez vs Dimitrov |
| 17 Aug 16 | r50 | Western and Southern Financial Group Masters Nadal vs Cuevas |
| 17 Aug 16 | r50 | Western and Southern Financial Group Masters Goffin vs Tomic |
| 17 Aug 16 | r50 | Western and Southern Financial Group Masters Johnson vs Benneteau |
| 17 Aug 16 | r50 | Western and Southern Financial Group Masters Kyrgios vs Coric |
| 18 Aug 16 | r50 | Western and Southern Financial Group Masters Gasquet vs Anderson |
| 18 Aug 16 | r50 | Western and Southern Financial Group Masters Cilic vs Verdasco |
| 18 Aug 16 | r50 | Western and Southern Financial Group Masters Berdych vs Granollers |
| 18 Aug 16 | r50 | Western and Southern Financial Group Masters Murray vs Monaco |
| 18 Aug 16 | r50 | Western and Southern Financial Group Masters Mahut vs Sugita |
| 18 Aug 16 | r50 | Western and Southern Financial Group Masters Thiem vs Monfils |
| 18 Aug 16 | r50 | Western and Southern Financial Group Masters Wawrinka vs Dimitrov |
| 18 Aug 16 | r50 | Western and Southern Financial Group Masters Tsonga vs Johnson |
| 18 Aug 16 | r50 | Western and Southern Financial Group Masters Nadal vs Coric |
| 18 Aug 16 | r50 | Western and Southern Financial Group Masters Nishikori vs Tomic |
| 18 Aug 16 | r50 | Western and Southern Financial Group Masters Raonic vs Sugita |
| 19 Aug 16 | r50 | Western and Southern Financial Group Masters Murray vs Anderson |
| 19 Aug 16 | r50 | Western and Southern Financial Group Masters Berdych vs Cilic |
| 19 Aug 16 | r50 | Western and Southern Financial Group Masters Johnson vs Dimitrov |
| 19 Aug 16 | r50 | Western and Southern Financial Group Masters Raonic vs Thiem |
| 19 Aug 16 | r50 | Western and Southern Financial Group Masters Cilic vs Coric |
| 20 Aug 16 | r50 | Western and Southern Financial Group Masters Murray vs Tomic |
| 21 Aug 16 | r50 | Western and Southern Financial Group Masters Murray vs Raonic |
| 21 Aug 16 | r50 | Western and Southern Financial Group Masters Cilic vs Dimitrov |
| 21 Aug 16 | r50 | Western and Southern Financial Group Masters Murray vs Cilic |
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