Lenny Rodrigues started off his career with Churchill Brothers and showed immense promise in his early days, helping the club win two I-League titles before moving to Pune FC in one of the biggest contracts given to an Indian player at that point of time.
In 2014, the 31-year-old was drafted by FC Pune City in the Indian Super League draft with their first pick. Lenny played three seasons in the ISL with the Stallions, interspersed with intermittent loans to Dempo, Mohun Bagan and Bengaluru FC.
The versatile midfielder has been a vital cog wherever he has played. He helped Mohun Bagan win the Federation Cup in 2016 and then won it again next season with Bengaluru FC. The Indian international made his move to Bengaluru permanent in 2017, helping them reach the final of the Indian Super League and win the Super Cup before repeating the feats with the Gaurs next season.