Gawli started his career at FC Kochin where he joined in 1998 after graduating from Tata Football Academy and won the Kerala League with them before moving on to Churchill Brothers.
He also helped them secure the Runners-up medals in the 2001–02 season of National Football League (India) before moving on to Kolkata biggies East Bengal.
[3] After a successful three-year stint with the East Bengal, it was time for Mahesh to find his place in Mahindra United team.
[4] Gawli has won two I-League titles with Dempo and is a regular starter for the club and forms a formidable partnership with another India international Samir Naik.
Gawli soon made his international debut in the pre-Olympic qualifier against Thailand in 1999 and cemented his place in the Indian team.