The Commissioner's Cup was a contest between the Whitecaps, who finished runner-up by one point, and the Puerto Rico Islanders.

The Whitecaps deservedly won the second leg 2-0 at home to go through 2-1 on aggregate to the final against Puerto Rico Islanders.

The playoff final was a back and forth game in which the Whitecaps prevailed 2-1 in front of 5,822 at their long time home of Swangard Stadium.

The Whitecaps finished third in the 2008 Voyaguers Cup with two losses to Montreal and a draw and a win over Division 1 MLS side Toronto FC.

Many local long time stalwart veteran players such as Jeff Clarke, Jason Jordan, Steve Kindel, Geordie Lyall, Martin Nash, and Alfredo Valente remained on the roster.