| 14 Oct 19 | r61  |  Kremlin Cup Garin vs Seppi |
| 14 Oct 19 | r61 | Kremlin Cup Londero vs Rosol |
| 14 Oct 19 | r61 | Kremlin Cup Mannarino vs Dzumhur |
| 15 Oct 19 | r61 | Kremlin Cup Berankis vs Carballes Baena |
| 15 Oct 19 | r61 | Kremlin Cup Kecmanovic vs Dubrivnyy |
| 15 Oct 19 | r61 | Kremlin Cup Kukushkin vs Donskoy |
| 15 Oct 19 | r61 | Kremlin Cup Herbert vs Kohlschreiber |
| 15 Oct 19 | r61 | Kremlin Cup Chardy vs Jarry |
| 15 Oct 19 | r61 | Kremlin Cup Bedene vs Karlovic |
| 15 Oct 19 | r61 | Kremlin Cup Rublev vs Bublik |
| 16 Oct 19 | r61 | Kremlin Cup Fabbiano vs Gerasimov |
| 16 Oct 19 | r61 | Kremlin Cup Avidzba vs Kachmazov |
| 16 Oct 19 | r61 | Kremlin Cup Seppi vs Carballes Baena |
| 16 Oct 19 | r61 | Kremlin Cup Mannarino vs Kukushkin |
| 16 Oct 19 | r61 | Kremlin Cup Lajovic vs Rosol |
| 16 Oct 19 | r61 | Kremlin Cup Khachanov vs Kohlschreiber |
| 17 Oct 19 | r61 | Kremlin Cup Milojevic vs Avidzba |
| 17 Oct 19 | r61 | Kremlin Cup Rublev vs Gerasimov |
| 17 Oct 19 | r61 | Kremlin Cup Kecmanovic vs Chardy |
| 17 Oct 19 | r61 | Kremlin Cup Cilic vs Karlovic |
| 18 Oct 19 | r61 | Kremlin Cup Lajovic vs Mannarino |
| 18 Oct 19 | r61 | Kremlin Cup Khachanov vs Seppi |
| 18 Oct 19 | r61 | Kremlin Cup Cilic vs Chardy |
| 18 Oct 19 | r61 | Kremlin Cup Rublev vs Milojevic |
| 19 Oct 19 | r61 | Kremlin Cup Mannarino vs Seppi |
| 19 Oct 19 | r61 | Kremlin Cup Cilic vs Rublev |
| 20 Oct 19 | r61 | Kremlin Cup Rublev vs Mannarino |
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