1987: two-year-old season After finishing unplaced over seven
furlongs on his racecourse debut, Ile de Chypre finished second to Highbrow in a sixteen-runner
maiden race over one mile at
Newmarket Racecourse in October. The independent
Timeform organisation commented "will be suited by 1¼m+: sure to win a race".
1988: three-year-old season After finishing second in the April Maiden Stakes on his three-year-old debut over one and a half miles, Ile de Chypre was sent to
Royal Ascot to contest the
King George V Stakes over the same distance on 16 June. He led from the start and looked likely to win before swerving abruptly to the left inside the final furlong and unseating his jockey
Greville Starkey. It was later claimed that the horse had been targeted by an "ultrasonic gun" as part of a
money laundering operation by a cocaine-smuggling syndicate. In a trial at
Southwark Crown Court in 1989 a car dealer named James Laming claimed that he had carried out the operation and that the device had been disguised as a pair of binoculars but was somewhat vague regarding the details. He continued to compete in major
handicap races, finishing second in the
Old Newton Cup at
Haydock Park and third in the
John Smith's Magnet Cup at
York before being dropped back in class and recording his first success as he won a maiden race at
Newbury Racecourse on 12 August by ten
lengths. In September he finished unplaced in the Garrowby Limited Handicap at York and then won sixteen-runner a handicap at Newbury, beating Quinlan Terry by three lengths. On his final appearance o the season he carried top weight of 134 pounds in the
Cambridgeshire Handicap on 1 October. He led for most of the way but was caught in the final strides and beaten a neck by Quinlan Terry who was carrying 117 pounds.
1989: four-year-old season Ile de Chypre began his third season by finishing unplaced when carrying top weight in the
Lincoln and then ran second under 140 pounds in a handicap at Newmarket. He was then stepped up in class and sent to Ireland to contest the
Group Two Tattersalls Rogers Gold Cup at the
Curragh on 20 May. Ridden by the
Welsh jockey Tony Clark he started at odds of
7/1 behind Executive Perk (
Mooresbridge Stakes), Per Quod (runner-up in the
Gordon Richards Stakes) and
Carroll House. He recorded his biggest win up to that time as he won by three lengths from Executive Perk with Carroll House a length and a half back in third. At
Epsom in June Ile de Chypre was promoted to Group One class for the
Coronation Cup and took the lead a furlong out before being overtaken and beaten half a length by the favourite
Sheriff's Star. The horse was dropped back in class and distance for the Group Three
Scottish Classic over ten furlongs at
Ayr Racecourse and was beaten by the three-year-old
Scenic. On 22 August Ile de Chypre was ridden by Clark when he was one of seven runners to contest the 18th running of the International Stakes over ten and a half furlongs at York.
Cacoethes, also trained by Guy Harwood was made the 2/5 favourite after finishing rthird to
Nashwan in
The Derby and second to the same horse in the
King George VI and Queen Elizabeth Stakes, whilst Ile de Chypre was a relative outsider on 16/1. The other five runners were Two Timing (
Prince of Wales's Stakes), Magic Gleam (
Child Stakes),
Shady Heights, Batshoof and Lapierre (
Prix Jean Prat). After tracking the leader Two Timing in the early stages Clark sent Ile de Chypre into the lead three furlongs from the finish and accelerated clear of the field. Cacoethes emerged as his only challenger but Ile de Chypre stayed on strongly to win by one and a half lengths with a gap of four lengths back to Shady Heights in third. On his retirement from race riding in 2004 Clark said "Ile de Chypre was a horse who took a lot of knowing but he was very game and I don't think he got the credit he deserved - he was a great favourite". After a break of two months, Ile de Chypre returned to the track in the
Champion Stakes at Newmarket on 21 October. Ridden by
Willie Carson he led for most of the way before being caught in the final strides and finishing third, beaten a head and short head by
Legal Case and Dolpour in a three-way
photo finish. Ile de Chypre ended his season with a trip to the United States for the
Breeders' Cup Turf at
Gulfstream Park on 4 November in which he finished unplaced behind
Prized.
1990: five-year-old season On his first appearance in 1990, Ile de Chypre finished second by a neck to Dolpour in the Gordon Richards Stakes at
Sandown Park Racecourse in April. Four weeks later he was sent to France and finished sixth of the nine runners behind Creator in the
Prix d'Ispahan. In the Eclipse Stakes at Sandown in July he led for most of the way before being outpaced in the closing stages and finishing third behind
Elmaamul and
Terimon. After a break of three months Ile de Chypre returned in a minor race at
Warwick Racecourse in October. Starting at odds of 1/6 he won by a length from Riviera Magic.
1992: seven-year-old season Ile de Chypre missed the whole of the 1991 season before returning as a seven-year-old in 1992. In April he finished third in the
Magnolia Stakes at
Kempton Park Racecourse and then finished unplaced in the Gordon Richards Stakes. In the summer of 1992 he finished fourth in the Scottish Classic and third in a handicap at York. In his last two starts he finished fifth in the
September Stakes and unplaced in a handicap at Newbury. ==Stud record==