Leander was born in Calcutta, India, on 17 June 1973 to Vece Paes, a Goan, and, Jennifer Paes, from Calcutta. He was educated at La Martiniere Calcutta, and the St. Xavier's College of the University of Calcutta. His parents were both sports persons. Vece was a midfielder in the bronze medal-winning Indian field hockey team at the 1972 Munich Olympics.

Paes started his Davis Cup career in 1990 at the age of 16, when he partnered Zeeshan Ali in doubles to beat the Japanese team in a gruelling five-set encounter. He is considered one of the top Davis cup players for his country, with a record of 89-32 overall, as of July 2015. He played an important role in the Indian Davis cup team that reached the World Group from 1991-1998. He was part of the Indian Davis Cup team that reached the semifinals of the 1993 Davis Cup with wins against Switzerland and France, eventually losing to Australia. In singles, his major wins came against French duo of Arnaud Boetsch and Henri Leconte in Frejus, France in 1993, Wayne Ferreira in 1994, and Goran Ivanisevic in 1995 when India defeated Croatia, Jan Siemerink in 1995 to defeat Netherlands, and Jiri Novak in 1997. He teamed up with Bhupathi to beat Hirszon and Ivanisevic of Croatia in 1995, Martin Damm and Petr Korda of the Czech Republic in 1997, Nicolas Massu and Marcelo Rios of Chile in 1997, Broad and Tim Henman in 1998, and Simon Aspelin and Jonas Bjorkman of Sweden in 2005. In 2007, Leander has three wins (two doubles and one singles) and no losses in the Davis Cup.  In 1993, ranked No. 197, he lost to No. 238 Fernon Wibierin the first round of qualifying at Wimbledon. Three weeks later he beat No. 25 Arnaud Boetsch on clay in straight sets in the Davis Cup. He also defeated Henri Leconte in the same week and even though Ramesh Krishnan closed the tie out by beating Rodolphe Gilbert in a five-setter, the architect of that victory was Paes.  In 1994, ranked No 143, he lost in the first round of a Challenger to No 208 Louis Gloria. Four weeks later, he beat World No. 13 Wayne Ferreira in straight sets in the Davis Cup.  In 1995, ranked No 130, he managed to beat Croatia's World No 7 Goran Ivanisevic (1992 and 1994 Wimbledon singles finalist) in a controversial five-setter on grass. Jan Siemerink, in 1996, then ranked No. 20, also fell to Paes in the Davis Cup.

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