I think the US/Trini thing has always been one of confidence or lack thereof. Post 11/89 is when they really became stronger/better than us. However I don't think that they have beaten us by more that one goal over the years (I might be wrong), but if I remember correctly, we were not exactly run over by them.
It would be nice(I think), to be drawn with them in the first round of the WC. To me, beating them in front of the world would finally put to rest the events of 11/89
Peace