From Pune, Deshpande made his first-class debut in December 1986, playing against Saurashtra in the 1986–87 Ranji Trophy.
[1] He scored his maiden first-class half-century during the 1990–91 season, making 60 against Gujarat.
[2] In the 1991–92 Ranji Trophy, Deshpande scored 465 runs from six games.
[3] In the first game of the tournament, against Gujarat, he scored 217 from 329 balls opening the batting with Surendra Bhave, putting on 287 for the second wicket with Santosh Jedhe.
[4] In the tournament's quarter-final, against Haryana, he scored 86,[5] but that was his last appearance for Maharashtra.