The USVIFA was formed in 1989 but didn't join FIFA untill 1998. Since then they#ve frequently occupied the bottom few places in the FIFA World Rankings, despite there being several countries with smaller populations. All three of the USVI wins have come against the neighbouring British Virgin Islands, most recently in the 2014 World Cup Qualifying.
US Virgin Islands - Home - ?
This shirt is another from Replay Football shirts.
"The USVI shirts were purchased from a contact in the USA. They are believed to be from a friendly match between USVI and the British Virgin Islands in a non-official (pre-FIFA) friendly. Apparently the shirts were initially given to the USVI by the BVI (hence the kit being made by Umbro). Approx year is 1990. I've been asking around for more detailed info and photos of the match but with no luck so far. I'll be in touch if I have anything."