Chandrasekhar was born in 1945 in Mysore, where he had his primary education. He developed an early interest in cricket watching the playing styles of Australian leg spinner Richie Benaud. An attack of polio at the age of six left his right arm withered. At the age of 10, his hand had recovered and Chandrasekhar started playing cricket.

By that time his family relocated to Bangalore and he got an opportunity to play for “City Cricketers”. In an interview, Chandrasekhar stated that he joined up mainly to get a chance to play with the leather ball. While playing on the streets of Bangalore, he had mainly used a rubber ball. While playing for the club, Chandrasekhar tried different bowling styles that also included fast bowling. It was in 1963 that he decided to play as a leg spin bowler. His idea proved to be right as he was soon selected for the national side.

Making his Test debut for India against England at Bombay in 1964, he collected four wickets in the match. He was named the Indian Cricket Cricketer of the Year the same year. Chandrasekhar was influential in setting up India’s first victory in England when he picked up six wickets for 38 runs at The Oval in 1971; the bowling was named the “Indian Bowling performance of the century” by Wisden in 2002. Wisden noted that, “[Chandrasekhar] was wonderfully accurate for a bowler of his type, and his extra pace made him a formidable proposition even on the sluggish Oval pitch.” His consistent bowling performances in 1971 earned him being named one of the five Wisden Cricketers of the Year in 1972.

In a Test against New Zealand in 1976, Chandrasekhar and Prasanna took 19 wickets and were crucial in setting up India’s win. Attributed to him is a famous umpire-directed quote, made during a day of bad decisions in New Zealand after several of his lbw appeals were given not out: “I know he is bowled, but is he out?” Chandrasekhar also played a major role in India’s victory in Australia in 1977–78.During that series he became the first bowler in test history to register the identical figures in a same test (6 for 52 in both innings).