As a played, Roomy played for the Sri Lanka national football team. After retiring from playing football, started his coaching career and he was appointed manager of Colombo FC and Zahira College, Colombo in 2010. At Colombo Football Club he was able to deliver their first trophy in 2010 and was instrumental in helping the club win the 2015 Sri Lanka FA Cup and the league three times in a row.[1] He obtained the AFC A Coaching License in 2020. In 2022, he was appointed manager of the Sri Lanka national football team, where he managed the team for 2023 AFC Asian Cup qualification.[2] However, during the third round, they finished last place in their group so were unable to achieve qualification for the tournament.
Following his stint there, he was appointed manager of the Sri Lanka women's national football team in 2024. Upon managing the team, Sri Lankan newspaper Ceylon Today described him as a "well-known figure in football circles and had an illustrious career, vast coaching experience and renowned in Sri Lankan football circles... recognized for his strategic prowess and knack for player development".[3] The Women's team went on to play for SAFF Women's Championship 2024 in Nepal and the first group game Sri Lanka team was victorious against Maldives National Women's Football team defeating them 1-0. This marked a significant achievement as the Sri Lanka women's football team is lacking a domestic league for more than 5 years and the improvement in such a short period was highly credited to Mr. Roomy for being able to get the best out of the player in merely 40 days.