The race was won by Persimmon, a bay colt by St Simon out of Perdita II trained by Richard Marsh at Newmarket. The colt brought the Prince of Wales, later Edward VII, the first of three victories in the Derby. Royalty had not won the Derby since 1788, when Sir Thomas, owned by the then Prince of Wales, later George IV, beat Lord Grosvenor's Aurelius, so this was an important achievement for the Royal colours.

Eleven runners went to post for the 1896 Derby. St Frusquin. a colt owned by Leopold de Rothschild, also by St Simon, was installed the 13-8 favourite, while Persimmon was 5-1 second favourite. As the starter raised his flag Bay Ronald was the first to show, followed by Bradwardine, Tamarind, Earwig, and Gulistan, with Persimmon and St Frusquin, ridden by Tommy Loates, the two backmarkers. With a mile remaining in the race St Frusquin reached the leaders, while Persimmon's jockey Jack Watts was happy to bide his time, edging closer and closer coming round Tattenham Corner. With just a quarter of a mile left Bay Ronald began to fade, leaving St. Frusquin in the lead. Watts asked Persimmon to quicken and he closed on the leader, but then suddenly he faltered. With under a furlong to go the experienced Watts, who had won the Derby three times before, steadied his mount, balanced him and drove him all the way to the line. Persimmon tenaciously forged his head in front to win by a neck in what was one of the most exciting Derbys of all time. The reception the Prince received as he led Persimmon into the winner's enclosure was a scene which those who witnessed it would never forget.

Richard Marsh paid tribute to the great Persimmon in his autobiography A Trainer to two Kings: 'A grander horse than Persimmon was as a four-year-old, especially on the day that he won the Gold Cup at Ascot, I never beheld. I would not have feared St Frusquin then, nor the greatest horse that ever walked the turf'.