Doriemus, one of just 11 horses to complete the Caulfield-Melbourne Cups double in the same year, has died aged 24.
The horse was euthanised at Melbourne's Living Legends retirement farm after suffering a hoof injury.
He was raced by a group which included Terry Henderson who is now in partnership with Simon O'Donnell in OTI Racing which announced his death on Twitter.
"Very saddened by death of Doriemus as result of hoof injury. An exceptional horse who gave many enjoyment while racing and in retirement," OTI said.
"At 24 Doriemus had a wonderful life in retirement thanks to Living Legends, Wingara Farm and Werribee Vet Hosp - all for their great care."
Doriemus won two of his first three starts in New Zealand for Jim Gibbs and was sent to Lee Freedman in 1994, winning his first Australian start for his new trainer that year in Brisbane.
As a four-year-old he won just two races but came into his own the following season to claim the 1995 Cups double.
He was unplaced in both races the following year and suffered a bleeding attack in the Australian Cup in March 1997.
He bounced back in the spring to finish a distant second to Might And Power in the Caulfield Cup before running the big horse to a nose in the Melbourne Cup.
Ironically the pair later shared a paddock at Living Legends.
Doriemus was retired after he was unplaced in the 1998 Melbourne Cup with a record of nine wins and 12 placings from 44 starts and prize money of almost $3.6 million.