Wolves only visit to the Caribbean came in late May 1964. On the tour Wolves faced three Caribbean Countries and Chelsea in a series of five matches. During the tour Wolves beat Trinidad 4-0 in Port of Spain – with Ray Crawford netted a hat-trick – Jamaica 8-4 in Kingston and Haiti in Port-au-Prince, a game that ended 1-1 with Terry Wharton scoring Wolves solitary goal. The series of matches against Chelsea saw Wolves win two and lose three. The series began with a match in Bridgtown and saw Wolves win 3-1 before losing 3-2 in Port of Spain. They then faced each other twice in Kingston with Wolves winning one 4-2 and losing the other 3-0. They rounded of the tour in Port-au-Prince, losing 2-0.