Jamaica entered the final round of the 2010 Caribbean Cup after a 0–0 draw with Costa Rica. After finishing first in its group, Jamaica won against Grenada in the semi-finals, then defeating first-time finalists Guadeloupe in a penalty shoot-out. Jamaica earned its fifth title, and coach Theodore Whitmore became the first to win the Caribbean Cup as both player and coach. In the 2011 CONCACAF Gold Cup, Jamaica finished first in its group, beating Grenada 4–0, Guatemala 2–0, and Honduras 1–0 before being eliminated by the US, with goals from American players Jermaine Jones and Clint Dempsey.