In December 1954, while playing for Bombay against Pakistan Combined Services and Bahawalpur XI, he picked all ten wickets in an innings, returning figures of 10/78.
[2] In August 1955, Gupte picked up his second ten-wicket haul in an innings (10/101), playing for Rishton in the final of the Lancashire League Worsley Cup against Todmorden.
During the Third Test at the Feroz Shah Kotla in Delhi, the team stayed at the Imperial hotel, where Gupte was housed in room number 7 along with teammate A. G. Kripal Singh.
During the stay, a receptionist at the hotel lodged a complaint with the India team manager against inmates of that room accusing them of calling her over after her shift finished.
The pair denied the allegation, with Gupte, who was married at the time, explaining that Singh had merely called and asked for drinks to be brought up.
Gupte later recollected that, M. A. Chidambaram, the President of the BCCI during the time, did not give him a hearing in Calcutta, the venue of the Fourth Test, as promised.
Gupte met Carol at an official function during his successful 1952–53 tour of the Caribbean with India, which he finished claiming 50 first-class wickets.