He played a memorable inning in 1979 against Asif Iqbal's Pakistan team in the 2nd Test at Feroz Shah Kotla, Delhi.

With Yashpal Sharma, Kapil Dev and Roger Binny back to the pavilion after the Tea break, Vengsarkar saw himself running out of partners and decided to play the last few overs for a draw.

During the 1978–79 Test Series in India against the West Indies, he was involved in a partnership of over 300 runs with Sunil Gavaskar at Calcutta, with both batsman scoring centuries.

While the West Indies pacemen dominated the cricket world, Dilip Vengsarkar was one of the few batsmen who was successful against them, and scored 6 centuries against the likes of Malcolm Marshall, Michael Holding and Andy Roberts.

Vengsarkar took over the captaincy from Kapil Dev after the 1987 Cricket World Cup, despite criticism that he missed the semi-final match due to a stomach disorder resulting from a seafood allergy.

Although he started with two centuries in his first series as captain, his captaincy period was turbulent and he lost the job following a disastrous tour of the West Indies in early 1989 and a stand-off with the Board of Control for Cricket in India.

A Bollywood film 83 released in 2021 about the events around India's first World Cup win, at Lords in 1983, features Adinath Kothare as Vengsarkar.