Born in Leesville, Louisiana, Masters grew up on Long Island and graduated from The Wheatley School of Old Westbury, New York in 1985.

In 1991, Masters scored seven goals as the Capitals went to the APSL title game only to lose to the San Francisco Bay Blackhawks.

[5] At the end of the APSL season, Masters traveled to England for a trial with Colchester United which, after relegation the previous year, played in the GM Vauxhall Conference.

The Conference is the fifth tier of English soccer and, while classified as 'non-league', still received significant media coverage and support from fans.

A few days later, Masters headed the first goal in Colchester's 3–1 victory over Witton Albion in the FA Trophy final, sealing the so-called 'non-league' double for his side.

Despite Masters' productive time with Colchester, the British Home Office denied him a work permit and he returned to the United States.

[8] On June 27, 1992, Masters earned his only cap for the United States national team,[9] he replaced Eric Wynalda in the 59th minute of the 0–0 draw with Ukraine at Rutgers Stadium in Piscataway, New Jersey.