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Born in Kingston, Jamaica, Williams began his career in the youth ranks of St. George's College. While with St.George’s Williams led the school to two youth championships in 2008 and 2009. In 2010, he joined Real Mona F.C. and remained at the club through 2014. In 2011 Williams accepted an offer to play college soccer for Robert Morris Colonials. Williams was handed the number 10 shirt and in his four years with the Colonials he appeared in 71 matches scoring 6 goals and recording 15 assists. During the 2014 season Williams also played with Pittsburgh Riverhounds U23.

On July 6, 2016, he made his New York Red Bulls debut in a mid-season friendly against Mexican powerhouse Club America. The Red Bulls went on to win the match by a 2–0 score. On August 12, 2016 Williams scored his first goal of the season for New York in a 5–1 victory over Orlando City B.

After a lengthy trial with the club, Williams signed with New York Red Bulls II on July 8, 2015. He made his debut for the club on July 18, 2015, appearing as a starter in a 2–0 victory over Harrisburg City Islanders. The following week Williams recorded his first assist for New York, helping Red Bull II to a 4–3 victory over Richmond Kickers. On August 12, 2015, Williams recorded his second assist of the season when he spotted Stefano Bonomo with a perfect cross into the box which was headed in helping NYRB II to a 1–1 draw against Charlotte Independence. On August 22, 2015, Williams scored his first goal as a professional, helping New York to a 2–0 victory over Toronto FC II.

Williams has represented Jamaica at the U-20 national team level, making five appearances for his country. On August 11, 2010, he made his first international appearance with the senior national team, appearing in a 3–1 victory over Trinidad and Tobago.

Devon Chesterton “Speedy” Williams (born 8 April 1992) is a Jamaican professional footballer who plays as a midfielder for Louisville City FC in the USL Championship.