The draw for the tournament took place on February 2, 2011. The first two rounds were played as two-leg, aggregate-goal series. The away goals rule would be applied, and extra time and penalty shootout would be used to decide the winner if necessary. The defending champion, Puerto Rico Islanders, received a bye to the second round. The final round, which consists of the semifinals, the third-place match, and the final, were played as one-leg matches. The original schedule as announced by the CFU is as follows (however, many matches of the first two rounds were played outside the original schedule):
Round
1st leg
2nd leg
First round
March 9–11
March 18–20
Second round
April 12–14
April 22–24
Final round
May 25–29
It was originally announced that the final round would be played at Trinidad and Tobago. However, it was announced on May 12, 2011, that Guyana's Alpha United, one of the semifinalists, would host the final round at Providence Stadium in Providence, Guyana, with the semifinals on May 25, and the third-placed match and the final on May 27.
Preliminary phase
Elimination stage 1
The first round schedule was announced on March 2, 2011.