The First Round featured fourteen teams. The only first team of a club that had to compete in this round was FC Triesen, while the other two teams eligible for the first round, FC Triesenberg and FC Schaan, received a bye. The games were played on August 26 – 28, 2008.
The six winners of the First Round, along with the two teams who had received a bye, competed in the Second Round. The first teams of FC Balzers, USV Eschen/Mauren, FC Ruggell and FC Vaduz were all given a bye in this round. The games were played on September 17 and 19, 2008.