Milind is an avid sportsman. He started swimming at age of 6 and he has been an international level swimmer. He started representing Maharashtra from the age of 10 at various age groups before going on to represent his state at senior level where he went on to hold the national swimming championship (senior men's) title for four consecutive years (1984-87) before giving up competitive swimming in 1988. Soman represented India in swimming in the inaugural South Asian Games (then known as South Asian Federation Games) in 1984 held at Kathmandu where he won a Silver medal. In 2015, Milind completed the Ironman challenge in 15 hours and 19 minutes , in his first try. The triathlon includes a 3.8-km swim, a 180.2-km cycle ride and 42.2-km run raced in that order without a break which the participants are required to complete within 17 hours to win the title of 'Ironman'. The title 'Ironman' is given to every person who achieves the feat within the given time. Milind Soman and his then-girlfriend, Madhu Sapre, an ex-Miss India and model, attracted controversy in India, when the pair posed nude in a print ad for Tuffs Shoes. The social service branch of the Mumbai police had registered a case in August 1995 after Sapre and Soman posed in the nude, wearing only shoes and a python wrapped around them. Another case was filed under the Wildlife Protection Act against the advertising agency for illegal use of the python. The accused include the publishers and distributors of two magazines that featured the controversial ad, the advertising agency, the two models and the photographers. The case dragged on for 14 years, after which the courts acquitted the accused.