Ridden by Michael Hills who became his regular jockey, he finished unplaced behind the future St Leger Stakes winner Classic Cliche.
In early 1996, First Island's most important role appeared to be that of lead-horse and training companion to the Wragg stable's outstanding middle-distance performer Pentire.
Ridden by Ray Cochrane, he took the lead approaching the final furlong and drew clear of the opposition to win by two and a half lengths under top weight of 133 pounds.
[12] In June, the colt was sent to Royal Ascot for the ten furlong Prince of Wales's Stakes, then a Group Two race open to horses of three years of age and older, for which Michael Stoute's improving four-year-old Pilsudski was made favourite.
Hills appeared short of racing room in the final quarter mile but managed to drive the colt though a narrow gap before catching Charnwood Forest in the closing stages to win by a length, with the previous year's top-rated two-year-old Alhaarth in third.
[15] First Island moved back up in distance when he appeared at York again in August and finished second to Halling in the International Stakes over ten and a half furlongs.
On his final European start of the year he made little impression in the Champion Stakes in October, finishing fifth of the six runners behind Bosra Sham and Halling.
Although no European-trained horse had won the race, he started 9/5 favourite against eleven opponents, including runners from Hong Kong, Australia, New Zealand, Ireland, Japan and Singapore.
[18] When preparing for Royal Ascot, First Island sustained a career-ending injury, described as a "spiral fracture to the right cannon bone"[19] when training at Newmarket on 5 June.