Complex sentence: He won the Gold Cup eleven times in all, a record, and his last win came at the age of 88 in 1997-8, a remarkable 52 years after his first and 33 years after his penultimate success.
Split into simpler sentences: He won the Gold Cup eleven times in all, a record. His last victory was in 1997-8 at the age of 88, a remarkable 52 years after his first win and 33 years after his penultimate success.