The Cup had a great start when GENERAL TRONG II, winner of six races the previous year, took the inaugural running.

For three consecutive years from 1976, English maestro Lester Piggott made the race his own, winning the speedy BLUE STAR in 1976 and 1977 and GENTLE JIM in 1978.

Blue Star’s double strike was emulated by ADDED ADVANTAGE II (1982 and 1983) and JINGLE BELL IV (1984 and 1985).

In 1986, the Singapore Turf Club (SNTC) staged the Lion City Cup at set-weights, when BALIK PULAU II created an upset. This this format proved unpopular and was scrapped after just one season. It was then reverted to a handicap.

WAR PLAN's Cup in 1990 was beamed "live" to Hong Kong and in turn local racegoers were treated to a telecast of the Hong Kong Derby.

In 1991, the SNTC decided to stage the Cup at weight-for-age raised the prizemoney to S$250,000 but it produced an upset winner in OLYMPIC BOY, ridden by apprentice Saifudin Ismail.

Under the new format, FISCHER won the Cup twice, in 1997 and again in 1999, when the race was run for the last time at Bukit Timah.

At its new home at Kranji, SUPERB EFFECT scored consecutive wins in 2000 and 2001. Then it was another Charles Leck-trained sprinter CLASSIC MARCO who took the honours in 2002.