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