Paes, together with Mahesh Bhupathi, were the first pair in Open era history to reach the men's doubles finals of all 4 Grand Slams in the same calendar year (1999).

He is also the most decorated male tennis player in Asian Games history with 5 Golds and 3 Bronzes winning medals in every category (singles, doubles, mixed doubles and team event) and the highest Indian gold medal winning athlete across all sports in Asian Games history.

[9][10] Paes retired from professional tennis in 2020,[11] following his last Davis Cup tie in Croatia, with a world record 1295 weeks spent ranked in the Top 100 in men's doubles.

[15][16] Paes enrolled with the Britannia Amritraj Tennis Academy in Madras (Chennai)[17] in 1985, where he was coached by Dave O'Meara.

[24] His first successful year in the ATP circuit came in 1993, when he partnered with Sébastien Lareau to reach the US Open doubles semifinal.

[25] That year he made his best singles performance in a Grand Slam, losing in the third round of the 1997 US Open to Cédric Pioline after beating Carlos Costa and Arnaud Boetsch.

[32] The following year, Paes partnered with Sébastien Lareau for the Australian and Jan Siemerink for the French, losing in the first round on both occasions.

He began the 2010 season in good form, again winning the Australian Open mixed doubles title with Cara Black.

Paes and Štěpánek's 2012 Wimbledon tournament ended when the duo lost to Ivan Dodig and Marcelo Melo.

[53] Paes and Elena Vesnina reached the finals of the Wimbledon mixed doubles after beating Bob Bryan and Liezel Huber, 7–5, 3–6, 6–3[54] on 7 July.

[56][57] In the 2012 Summer Olympics, the Indian pair (Vishnu Vardhan) lost to French team Michaël Llodra and Jo-Wilfried Tsonga, 6–7, 6–4, 3–6.

[58] Paes and Štěpánek advanced to the finals at the 2012 US Open after their Spanish opponents, Marcel Granollers and Marc López, retired because of injury.

[61] Paes and Štěpánek kicked off the ATP World Tour Finals with a win against Pakistan's Aisam-ul-Haq Qureshi and Dutchman Jean Julien Rojer, 6–4, 7–5.

[65] and later went on to make the semi-finals of Wimbledon in men's doubles with Štěpánek Paes started his 25th season on the ATP World Tour by partnering with Klaasen to reach the Chennai final, where the team lost to Lu/Marray.

On 1 February, Paes captured his seventh Grand Slam mixed doubles crown at the 2015 Australian Open with Martina Hingis.

The pair crashed out in the third round; however, Paes became just the seventh male player in Open Era to complete 700 doubles wins.

[67][68] On 12 September 2015, Paes won the mixed doubles at the 2015 US Open with Hingis, defeating Sam Querrey and Bethanie Mattek-Sands in three sets.

On 3 June 2016, Leander Paes completed his Career Grand Slam in mixed by winning the 2016 French Open with Hingis, thus joining an elite league of players.

[71] He turned up for the Davis Cup against Spain with Saketh Myneni, losing to Rafael Nadal and Marc López in 4 sets.

The duo lost to the Indian pair of Purav Raja and Divij Sharan in the first round of Aircel Chennai Open in straight sets.

Paes continued his partnership with Raja, losing the Maharashtra Open in the first round to defending champions Bopanna/Jeevan Nedunchezhiyan.

During the season, Paes made the semi-finals of three ATP 250 tournaments (Montpellier, Marrakesh and Lyon) with Benoit Paire.

He become the oldest ATP Tour semi-finalist since 2006 when he reached the semi-finals of the Hall of Fame Championship with Marcus Daniell in July 2019.

[75] Paes started his Davis Cup career in 1990, when he partnered Zeeshan Ali in doubles to beat the Japanese team in a five-set encounter.

He was part of the Indian team that reached the semifinals 1993 with wins against Switzerland and France, eventually losing to Australia.

They reunited to play in a Grand Slam Tournament after nine years and claimed runners-up in the 2011 Australian Open and reached the semifinals in the year-end championships.

[96] Paes threatened to withdraw from the Olympics rather than play with Vardhan, whose world ranking was 296,[97] but withdrew the threat a week later.

In 2021, Zee5 produced a documentary called Break Point, showing the ups and downs in the relationship between Paes and Bhupathi.

[99] In 2010, he joined the Board of Directors of Olympic Gold Quest,[100] a foundation co-founded by Geet Sethi and Prakash Padukone to support talented Indian athletes.

[102] By winning the 2012 Australian Open title, Paes achieved the career Grand Slam in mens doubles.