1897: two-year-old season In the spring of 1897, Cyllene won small races at
Liverpool and Gatwick "in good style". He was then sent to Ascot for the Triennial Stakes where he defeated
Nun Nicer, a filly who won the following year's
1000 Guineas, establishing himself as one of the best of an apparently "above the average" generation. At
Sandown in July he won the National Breeders' Produce Stakes by a head to take one of the season's most valuable two-year-old prizes, despite being unable to obtain a clear run until the closing stages. After a break of three months he returned to the racecourse in October for the Imperial Produce Stakes at
Kempton Park Racecourse in which he narrowly failed to give ten
pounds to Dieudonne, a colt who went on to win the
Middle Park Stakes later in the month.
1898: three-year-old season As he was ineligible to run in the Classics, Cyllene's three-year-old campaign was somewhat restricted. He was disappointing on his debut, finishing third at odds of 2/11 in the Column Produce Stakes at
Newmarket in April but was never beaten again. In May he easily won the
Newmarket Stakes by four lengths in record time, and was then rested until autumn. Before he returned, the form of his Newmarket win was boosted when
Jeddah, who had finished fifth in the race, won
The Derby. In September he produced his best performance to date to win the Jockey Club Stakes at Newmarket by six lengths from a field which included Dieudonne and the Classic winners
Airs and Graces and
Chelandry. On his final start of the year he won the Sandown Park Foal Stakes by four lengths,
1899: four-year-old season Cyllene's four-year-old season was compressed into a three-day period in June at
Royal Ascot. At the start of the meeting he won the Triennial Stakes which served as a warm-up for the Ascot Gold Cup two days later. Racing over two and a half miles in the Gold Cup, Cyllene turned the race into a "procession", taking the lead two furlongs out and pulling clear to win by eight lengths from Lord Edward and the
Prix du Jockey Club winner
Gardefeu. According to one correspondent, Cyllene "simply played" with the top quality field, with his jockey Sam Loates having time to stroke the horse's neck and touch his cap to the cheering crowd in the closing stages. The effects two races on firm ground meant that Cyllene's connections abandoned plans to run him for a third time at the meeting (in the
Hardwicke Stakes) and the colt was given an extended rest. In autumn there was much anticipation of a meeting between Cyllene and the
Triple Crown winner
Flying Fox, with Charles Day Rose being reported as saying that he "looked forward to beating" the outstanding three-year-old in the
Champion Stakes at Newmarket. When Cyllene returned to serious training however, it was decided that the risk of the horse breaking down was too great and he was retired to stud without racing again. ==Assessment==