The independent Timeform organisation gave him a rating of 111, twenty-one pounds behind their top-rated juvenile Huntingdale and described him as a "genuine" colt who was very well suited by soft ground.
[5] On his first appearance as a four-year-old Handsome Sailor finished third to the David Elsworth-trained Governor General in the Abernant Stakes over six furlongs at Newmarket in April.
[5] At Royal Ascot in June Handsome Sailor contested the Cork and Orrery Stakes and finished third behind Big Shuffle and Ongoing Situation.
Ridden by the Australian jockey Ron Quinton, Handsome Sailor lead for most of the way and rallied after being headed in the closing stages to win by three quarters of a length from Tenue de Soiree.
He returned to France for the Prix Maurice de Gheest at Deauville Racecourse in August but after leading with 400 metres left to run he finished fourth behind the British-trained filly Interval.
In the Haydock Sprint Cup on 5 September he was ridden by his trainer's son Michael Hills and finished third behind Ajdal and Sharp Romance, with Interval in fifth.
He began his campaign by finishing third to Dawn's Delight and Cragside in the Cammidge Trophy at Doncaster on 26 March before attempting to repeat his 1987 success in the Duke of York Stakes.
[8] For the second year in succession, Handsome Sailor was beaten in the Cork & Orrery Stakes at Ascot in June, finishing sixth behind the three-year-old filly Posada.
On 18 August at York Handsome Sailor was one of twelve horses to contest the Group One William Hill Sprint Championship and started the 5/2 favourite ahead of Perion and the three-year-old filly Silver Fling (winner of the King George Stakes).
The other runners included Cadeaux Genereux, Gallic League, Colmore Row (Norfolk Stakes) and Rotherfield Greys (Stewards' Cup).
His eight opponents included Big Shuffle, Cadeaux Genereux, Silver Fling, Sharp Romance, Caerwent (International Stakes), Bluebook (Prix de Seine-et-Oise) and La Grande Epoque (runner-up in the race in 1987).
The local stewards however, found that the "winner" had caused interference in the early stages: Cadeaux Genereux was disqualified and the race awarded to Handsome Sailor.
Starting at odds of 5/1 he got the better of a prolonged struggle with the Mark Prescott-trained filly Teeming Shore to win by a head, with a gap of three lengths back to Regal Peace.