The 1827 St. Leger was a particularly famous race and represented a major encounter in the long-running battle between North (represented by Matilda) and South (represented by Mameluke) - a poem by the Professor of Poetry at Oxford celebrating Matilda's win runs to over two hundred lines.
Bred by the Hon. Edward Petre, Matilda was by Comus out of Juliana. Her St. Leger win over Mameluke (by a length) was her greatest victory and was commemorated by Petre through the erection of a chiming clock over his stables at Stapleton Park, Yorkshire. Her jockey, James Robinson, rode her without spurs as portrayed in the present picture. Mameluke, by Partisan out of Miss Sophia was bred by Mr Elwes. He was sold to the Earl of Jersey for whom he won the Derby in 1827 with Robinson up. He was then sold to Mr. John Gully, the famous ex-prizefighter, for 4,000 guineas, and was ridden by Sam Chifney in the St. Leger depicted.
Matilda was very much the underdog at 10-1, while the much larger Mameluke was originally favourite at 5-2 until he became worked up by a series of false starts, engineered with this effect in mind. He eventually started at 100-30. Matilda was actually Petre's second string as he also owned Granby (who, after the false starts, started as favourite), ridden by Will Scott and also trained by John Scott. This is the reason that Matilda actually carried black, white sleeves, white cap, in the race, rather than the normal colours of black and pink in which the jockey is shown in the present picture. Major Yarburgh's Laurel finished third.
Herring painted several portraits of Matilda, including one in the collection of the Jockey Club, which are among his finest pictures. His work provides wonderful documentation of the history of the turf in the first half of the 19th Century, and a flattering review of Herring's paintings in The Annals of Sport in 1822 attests to his reputation: 'We were struck by the exquisite accuracy of the likenesses, and charmed by the colouring, the shades and the character thrown into each animal and its rider... and we may safely predict from these specimens that he will at no distant period rank with the most celebrated animal painters the country has ever patronized' (O. Beckett, J.F. Herring, London, 1981, p. 36).