Shashank Singh started playing cricket since 2008 playing for the under 19 teams in Mumbai. Shashank Singh later joined DY Patil which became his second home. Over the years Shashank Singh developed himself into a solid top-order batsman who became a backbone in DY Patil’s batting line up.

Shashank Singh made his List A debut in December 2015 in the 2015–16 Vijay Hazare Trophy and has also featured for the Delhi Daredevils in the 2017 Indian Premier League. While he did not play for the Daredevils, Shashank Singh gained valuable experience from team lead Zaheer Khan and coach Rahul Dravid. Most recently, Shashank Singh played for the Mumbai North East team in the inaugural T20 Mumbai League, winning the trophy with some powerful performances.