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 is highly regarded as one of the top free-kick specialist in the Jamaica National Premier League.

After a successful trial in early 2009, Woodbine joined the USL First Division side Charleston Battery for the 2009 season on 18 March 2009.

He made his senior national team debut for the Reggae Boyz on 26 March 2008, in a friendly against Trinidad and Tobago,[12] and played in Jamaica's qualifying games for the 2010 FIFA World Cup against the Bahamas,[13] Canada[14] and Honduras.

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.