In January 2014, Delwinder joined Courts Young Lions while serving his compulsory national services.
Delwinder was left without a club in 2015 after he was released by the Young Lions as his NS obligations meant that his unpredictable schedule made it hard for him to attend training regularly.
[5] After making over 40 starts in league and cup competitions for the Cheetahs, Delwinder was handed a contract extension for the 2017 S.League season.
On 6 August 2023, he make his debut for the club in a league match against ISI Dangkor Senchey.
[7] He became one of the youngest player to represent the Lions when he made his debut for the senior team against Philippines at the age of 18.