Born in Cortalim, Goa, began to develop a passion for football when his grandfather took him to watch local matches.
[1] On 22 July 2014, Rodrigues was selected as the first ever pick in the 2014 ISL Inaugural Domestic Draft by Pune City.
[6] After the conclusion of the 2016 ISL season, Rodrigues was loaned out to another I-League side, Bengaluru, on 15 December 2016.
[8] On 23 July 2017, Rodrigues was selected in the 8th round of the 2017–18 ISL Players Draft by Bengaluru for the 2017–18 Indian Super League season.
[10] On 20 April 2018, Rodrigues earned his only trophy for the club as a permanent player when he started for Bengaluru in their 4–1 victory over East Bengal in the Super Cup.
[12] During the 2018–19 ISL season Lenny, along with Ahmed Jahouh formed a solid midfielding partnership for FC Goa.
[14] Churchill Brothers[16] Mohun Bagan[16] Bengaluru[16] India[16] In January 2020, he got married and lives in Goa.