Complex sentence: Until 2008 Puerto Rico had not fielded a national team since 2004 when they lost to Grenada 5-2, the last time they had won a match was back in 1993 when they won 4-0 against the Cayman Islands.
Split into simpler sentences: Until 2008 Puerto Rico had not fielded a national team since 2004 when they lost to Grenada 5-2. The last time the Puerto Rico select won a match was back in 1993 when they won 4-0 against the Cayman Islands.