Florida Pearl made his final appearance of that season in April in the Punchestown Gold Cup, where he was once again sent off the odds-on favourite and finished a 14-length 2nd to Imperial Call.
He began the 1999–00 season in the Grade 1 James Nicholson Wine Merchant Champion Chase, which he won from Doran's Pride by 2½ lengths.
In a race which was marred by the subsequent death of the then-race leader Gloria Victis, Florida Pearl was unsuccessful in his bid to win the Cheltenham Gold Cup, finishing a 5-length second to fellow 9/2 joint favourite Looks Like Trouble.
The 2001/02 season proved to be a lot more successful for Florida Pearl, although it began with a 2½ length 3rd behind Foxchapel King in the James Nicholson Wine Merchant Champion Chase.
He exacted revenge on Native Upmanship from the previous season with a short head win in the John Durkan Memorial Chase.
Florida Pearl then returned to Kempton for the King George VI Chase in December, where he again exacted revenge on last year's winner, First Gold, with a 3/4 length victory over Best Mate.
He went back to Leopardstown to contest the Irish Hennessy for the 4th successive season, where he was sent off the 6/4 favourite and finished a 25-length 4th behind the winner and stablemate Alexander Banquet.
He began the season in January 2004, where he made a successful return to action at Fairyhouse in the Grade 3 Norman Grove Chase, running out a 2-length winner over Rince Ri.
In his final race, Florida Pearl returned to Leopardstown to contest the Irish Hennessy one last time, where he was sent off the 5/1 fourth favourite in the betting under jockey, Richard Johnson.