The MetroStars selected Miles in the second round in the 1996 MLS College Draft. He was with the MetroStars until they traded him to the Columbus Crew on May 3, 2000 for a second round 2001 draft pick. Joseph finished the 2000 season with Columbus before being traded to the Dallas Burn for the 2001 season. At the end of the season, the Burn released him. On February 13, 2003, the Dallas Sidekicks signed Miles as a free agent. He played only seven games with the Sidekicks in the 2002–03 season before leaving the team to become an assistant coach with the Siena College women’s soccer team on August 5, 2003. Miles served four years as an assistant coach for Major League Soccer's Real Salt Lake. Jason Kreis, the New York City FC head coach who knew Joseph from their times working together at Real Salt Lake, named Miles Joseph as the first assistant coach of New York City FC in 2014. New York City FC debuted as a club in the 2015 Major League Soccer season. On November 2, 2015 New York City FC, disappointed with not making the 2015 MLS Cup Playoffs, announced they had parted ways with Head Coach Jason Kreis as well as Joseph and assistant C. J. Brown after just one year of management and would be looking for a new head coach for the following season.
National teams
Joseph was selected for the roster of the U.S. team at the 1993 U-20 World Cup held in Australia. He scored a goal in the 6–0 victory over Turkey. The U.S. went 1–1–1 in group play, qualifying for the second round where it fell to Brazil. In 1996, U.S. coach Bruce Arena named Joseph to the U.S. soccer team at the 1996 Summer Olympics. Once again, the team went 1–1–1, but this time failed to make the second round. Joseph earned his first cap with the U.S. national soccer team when he came on for Cobi Jones in the 89th minute of a 3–1 win over El Salvador on August 30, 1996. He was again a late game substitute on December 21, 1996 in a 2–2 tie with Guatemala. He started his last national team game, a 2–1 loss to China, before coming off at halftime for Cobi Jones. Miles has now joined the technical coaching staff for Real Salt Lake. Prior to joining RSL, he was the technical and coaching director for Players Soccer Academy and the executive director for the New York Elite soccer program in the Clifton Park, New York area.