| 2026 | Fils A. | Tiafoe F. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 13 Aug 2026 – 23 Aug 2026 |
| 2025 | Alcaraz C. | Sinner J. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 7 Aug 2025 – 18 Aug 2025 |
| 2024 | Sinner J. | Tiafoe F. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 12 Aug 2024 – 19 Aug 2024 |
| 2023 | Djokovic N. | Alcaraz C. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 13 Aug 2023 – 20 Aug 2023 |
| 2022 | Coric B. | Tsitsipas S. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 14 Aug 2022 – 21 Aug 2022 |
| 2021 | Zverev A. | Rublev A. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 15 Aug 2021 – 22 Aug 2021 |
| 2020 | Djokovic N. | Raonic M. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 22 Aug 2020 – 29 Aug 2020 |
| 2019 | Medvedev D. | Goffin D. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 11 Aug 2019 – 18 Aug 2019 |
| 2018 | Djokovic N. | Federer R. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 12 Aug 2018 – 19 Aug 2018 |
| 2017 | Dimitrov G. | Kyrgios N. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 13 Aug 2017 – 20 Aug 2017 |
| 2016 | Cilic M. | Murray A. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 15 Aug 2016 – 21 Aug 2016 |
| 2015 | Federer R. | Djokovic N. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 16 Aug 2015 – 23 Aug 2015 |
| 2014 | Federer R. | Ferrer D. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 10 Aug 2014 – 17 Aug 2014 |
| 2013 | Nadal R. | Isner J. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 11 Aug 2013 – 18 Aug 2013 |
| 2012 | Federer R. | Djokovic N. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 12 Aug 2012 – 19 Aug 2012 |
| 2011 | Murray A. | Djokovic N. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 14 Aug 2011 – 21 Aug 2011 |
| 2010 | Federer R. | Fish M. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 15 Aug 2010 – 22 Aug 2010 |
| 2009 | Federer R. | Djokovic N. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 17 Aug 2009 – 23 Aug 2009 |
| 2008 | Murray A. | Djokovic N. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 28 Jul 2008 – 3 Aug 2008 |
| 2007 | Federer R. | Blake J. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 13 Aug 2007 – 19 Aug 2007 |
| 2006 | Roddick A. | Ferrero J.C. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 14 Aug 2006 – 20 Aug 2006 |
| 2005 | Federer R. | Roddick A. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 15 Aug 2005 – 21 Aug 2005 |
| 2004 | Agassi A. | Hewitt L. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 2 Aug 2004 – 8 Aug 2004 |
| 2003 | Roddick A. | Fish M. | Western & Southern Financial Group Masters 1000 | Cincinnati, Hard | 11 Aug 2003 – 17 Aug 2003 |
| 2002 | Moya C. | Hewitt L. | Cincinnati TMS 1000 | Cincinnati, Hard | 5 Aug 2002 – 5 Aug 2002 |
| 2001 | Kuerten G. | Rafter P. | Cincinnati TMS 1000 | Cincinnati, Hard | 6 Aug 2001 – 6 Aug 2001 |
| 2000 | Enqvist T. | Henman T. | Cincinnati TMS 1000 | Cincinnati, Hard | 7 Aug 2000 – 7 Aug 2000 |