Woodbine attended and played soccer at Frome Technical High School in his native Jamaica, He also represented National Premier League team Reno for under-21 and senior teams.Woodbine went on to join the USL First Division side Charleston Battery on loan and played in 16 matches for the Battery in 2009. Woodbine returned to Jamaica to represent Reno F.C. for the 2010-2011.
Woodbine joined the Finnish Veikkausliiga side Vaasan Palloseura for one plus one year contract on 25th February 2011. Woodbine is highly regarded as one of the top free-kick specialist