Woodbine attended and played soccer at George's Plain Primary School and Frome Technical High School in his native Jamaica, where he won the Westmoreland primary school league and DaCosta Cup. He started his club career at Reno of the Jamaican National Premier League where, under the tutelage of former Jamaican national team player and coach, Wendell Downswell, he played for under-21 and senior teams. At the conclusion of the USL-1 season, Woodbine returned to Jamaica to play for Reno in the 2009-2010 Western Confederation Super League, under coach Wendell Downswell. Woodbine has returned to Charleston Battery for the 2010USL-2 season. After winning the USL2 title with Charleston, Woodbine rejoin Reno F.C. for the 2010-2011 Jamaican National Premier League season. Woodbine is highly regarded as one of the top free-kick specialist in the Jamaican National Premier League.
United States
After a successful trial in early 2009, Woodbine joined the USL First Division side Charleston Battery for the 2009 season on 18 March 2009. Woodbine featured in 16 matches for the Battery in 2009.
Finland
After a successful trial in February 2011, Woodbine joined the Finnish Veikkausliiga side Vaasan Palloseura for one plus one-year contract on 25 February 2011. In August 2011, Woodbine went on loan to HJK Helsinki. Woodbine went 90 minutes in his debut for HJK in September 2011. After spending three months on loan to HJK, Woodbine's purchase option was declined. VPS picked up Woodbine option for the 2012 season. In 2013, Woodbine returned to Reno in the Jamaica Western Super League.
Woodbine signed with former club Charleston Battery in March 2015.
International
Woodbine is a member of the Jamaica national football team. He was a standout player on the U17, U20, U23 national teams since 2005. He made his senior national team debut for the Reggae Boyz on 26 March 2008, in a friendly against Trinidad and Tobago, and played in Jamaica's qualifying games for the 2010 FIFA World Cup against the Bahamas, Canada and Honduras. Woodbine also played in two matches for Jamaica during 2008 DigiceRenol Cup tournament. After a strong performance in the first round of the DPL season, Woodbine earned a recalled to the senior national team and was named to the 2010 Digicel Cup squad for Jamaica.
