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Thomas Enqvist won the title in 1996 after beating Byron Black 6-2,7-6 in the final.
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In 1997, Mikael Tillstrom defeated Alex Radulescu 6-4, 4-6, 7-5 to win the singles event.
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In 1998, Top seed Patrick Rafter won the title after defeating the defending champion Mikael Tillstrom 6-3, 6-4.
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Byron Black of Zimbabwe rose to fame with a 6-4, 1-6, 6-3 victory over German Rainer Schuttler in 1999.
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Frenchman Jerome Golmard beat Markus Hantschk of Germany 6-3, 6-7(6-8), 6-3 to claim the singles title in 2000.
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Jerome Golmard won the 2001 title defeating another first-time finalist Andrei Stoliarov 6-2, 7-6(7-4).
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Top seed Guillermo Canas outlasted Thailand's Paradorn Srichaphan 6-4, 7-6 to take the title in 2002.
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Crowd favourite Paradorn Srichaphan won his third ATP tour title thrashing Karol Kucera of Slovakia 6-3 6-1. The win came in 2003.
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Carlos Moya of Spain defeated Thai star Paradorn Srichaphan 3-6, 6-4, 7-6 (7-5) to win his first Chennai Open title in 2004. He succesfully defended the title in a repeat final.
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Croatian Ivan Ljubicic defeated twice defending champions Carlos Moya to lift the Chennai Open title in 2006.
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In 2007, Xavier Malisse created history by being the first to win both the singles and doubles title in Chennai.
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Mikhail Youzhny defeated Carlos Moya to take the Chennai Open title in 2008.
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Marin Cilic won back-to-back titles in 2009 and 2010.
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Stanislas Wawrinka is the most successful player in Chennai, capturing the title in 2011, 2014, 2015, and 2016.
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Canadian Milos Raonic upstaged top seed Janko Tipsarevic 6-7, 7-6, 7-6 to take the singles crown in a marathon match that lasted three hours and 16 minutes.
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Janko Tipsarevic defeated Roberto Bautista-Agut 3-6, 6-1, 6-3 to win the title in 2013.
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Roberto Bautista Agut defeated Daniil Medvedev to clinch the title in 2017, which turned out to be the last edition in Chennai.
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