When was the Winter Derby established?

Not to be confused with the historic Derby Stakes, which is, of course, run over a mile and a half at Epsom on the first Saturday in June, the Winter Derby Stakes is run over a mile and a quarter on the essentially sharp, left-handed all-weather track at Lingfield in February or March. Unlike the Derby proper, which is restricted to three-year-old colts and fillies, the Winter Derby is open to horses of both sexes, including geldings, aged four years and upwards. The all-weather track at Lingfield, which was originally Equitrack, but has been Polytrack since 2001, is not dissimilar to Epsom, insofar as it is undulating, with a downhill turn into the straight, reminiscent of the famous Tattenham Corner.

The Winter Derby was established, as a conditions stakes race, in 1998, but was promoted to Listed status the following year and, again, to Group 3 status in 2006, such that it is now the first Group race in the British Flat racing calendar and one of just four run on synthetic surfaces. The 2023 winner, Lord North, who justified odds-on favouritism with a ready, 3¼-length win, was the highest-rated horse ever to compete in the Winter Derby. Unsurprisingly, though, his winning prize money, of £56,710, was just a fraction of the £885,781 taken home by the Derby winner, Auguste Rodin.

The inuaugural winner of the Winter Derby was the four-year-old Running Stag, trained by Philip Mitchell, in Epsom, and ridden by Ray Cochrane. The son of Breeders' Cup Mile winner Cozzene won comfortably, by 3½ lengths, from Refuse To Lose and Mitchell later reflected on his success, saying, 'That was a serious coup. He was a Group horse racing against good handicappers.' Later that season, Running Stag competed in Germany, France and the United States, finishing seventh in the Breeders' Cup Classic at Churchill Downs.

Generally speaking, how have fillies fared in the Derby?

Of course, the Derby Stakes was famously founded by Sir Charles Bunbury and Edward Smith-Stanley, the Twelfth Earl of Derby, in 1780 and reputedly named in honour of the latter after a (probably apocryphal) coin toss between the pair. The race has always been run at Epsom Downs Racecourse in Surrey, but the first four renewals were staged on a straight, one-mile course; the wide, sweeping, left-handed turn into the straight, known as Tattenham Corner, did not become a feature of the Derby course until 1784, when the distance was extended to a mile and a half. Similarly, the Derby has always been open to three-year-old thoroughbred colts and fillies, although nowadays the race conditions stipluate 'entire' colts only; geldings have been excluded since 1904.

The Derby is the most prestigious of the five British Classics – the other four being the 2,000 Guineas, 1,000 Guineas, Oaks and St. Leger – and, with the winner collecting £892,160, at the last count, far and away the most valuable. Despite being run on the famously undulating, switchback track at Epsom, the Derby is supposed to produce a winner that is the outstanding middle-distance performer of a generation, whose name is, accordingly, etched into the annals of racing history. Nevertheless, for all the prestige and value of the 'Blue Riband' event, the names of winning fillies on the Derby roll of honour are few and far between, especially since the turn of the twentieth century.

In fact, the last filly to contest, never mind win, the Derby was Cape Verdi, way back in 1998. Owned by Goldolphin and trained by Saeed bin Suroor, the daughter of Caerleon, from the family of Nijinsky, justified joint-favouritism in the 1,000 Guineas when hacking up by 5 lengths on her first outing in the now-famous royal blue silks. Consequently, she was sent off as clear 11/4 favourite at Epsom, ahead of Grand Criterium winner Second Empire, trained by Aidan O'Brien, but, in truth, never really figured. Held up early, she met trouble in running on the descent into Tattenham Corner, but looked a non-stayer as she weakened inside the final quarter of a mile, eventually finishing ninth of 15, 12 lengths behind the eventual winner, High-Rise.

Overall, in 244 runnings of the Derby, so far, including the substitute races run at Newmarket between 1915 and 1918, during World War I, and between 1940 and 1945, during World War II, just six fillies – or, in other words, less than 0.25% of all the winners – have been victorious. The first of them was Eleanor, owned by the aforementioned Sir Charles Bunbury, in 1801 and she followed, in chronological order, by Blink Bonny in 1857, Shotover in 1882, Signorinetta in 1908, Tagalie in 1912 and Fifinella in 1916. The last-named, trained by Richard 'Dick' Dawson, won the so-called 'New Derby Stakes' at Newmarket on May 30, 1916 and followed up in the 'New Oaks Stakes', over the same course and distance, two days later. Thus, the last filly to win an 'authentic' Derby, over the traditional course and distance on Epsom Downs, was Tagalie in 1912.

Notwithstanding the existence of the Oaks Stakes, run over the same course and distance as the Derby, the dearth of fillies in the principal Classic essentially boils down to the commercial realities of the bloodstock industry. A colt that wins the Derby can command eye-watering stud fees as a stallion and, potentially, cover hundreds of mares a year. The 2009 Derby winner, Sea The Stars, for example, is currently standing at the Gilltown Stud, in Kilcullen, Co. Kildare for €200,000. By contrast, a filly that wins the Derby can only produce one foal a year as a broodmare and, as such, is a much less valuable commodity.

Which is more difficult to win, the British or American Triple Crown?

For the uninitiated, the British, or English, Triple Crown consists of the 2,000 Guineas Stakes, run over a mile at Newmarket in early May, the Derby Stakes, run over a mile and a half at Epsom Downs on the first Saturday in June, and the St. Leger Stakes, run over a mile and three-quarters at Doncaster in September. The American Triple Crown, on the other hand, consists of the Kentucky Derby, run over a mile and a quarter at Churchill Downs on the first Saturday in May, the Preakness Stakes, run over nine and a half furlongs at Pimlico two weeks later, and the Belmont Stakes, run over a mile and a half at Belmont Park three weeks after that.

In both cases, all three constituent races are open to three-year-old colts and fillies so, aside from obvious disparities in terms of distance and timing, the main difference is that the British series is contested exclusively on turf, whereas the American series is contested exclusively on dirt. Chronologically, the British Triple Crown pre-dates the American Triple Crown by 66 years, by virtue of the fact that the constituting races have co-existed since 1809, as opposed to 1875.

The first horse to win the British Triple Crown was West Australian in 1853 and, since then, a total of 15 horses have done so. However, it is important that the most recent of them was Nijinsky in 1970 and, since then, only three horses – Nashwan, in 1989, Sea The Stars, in 2006, and Camelot, in 2012 – have won both the 2,000 Guineas Stakes and the Derby Stakes; the first two named were not even entered in the St. Leger Stakes, emphasising the preference for speed over stamina in the modern bloodstock market. On the other side of the Atlantic, a total of 13 horses have won the American Triple Crown, the most recent being Justified in 2018.

Notwithstanding the declining popularity of the British Triple Crown, which series is more difficult to win is, largely, a matter of opinion. However, the general consensus is that the British Triple Crown, which requires a horse to reproduce its form over a matter of months, rather than weeks, over a wider range of distances, is the more demanding.

Which was the last filly to win the St. Leger Stakes?

Run annually over 1 mile, 6 furlongs and 115 yards on Town Moor, Doncaster in September, the St. Leger Stakes is the final British Classic of the season. The race is open to three-year-old colts and fillies and, as such, forms the final leg of the Triple Crown and the Fillies' Triple Crown, although the latter has not been won since 1970 and the latter not since 1985.

In the better part of two and a half centuries since the inaugural running of the St. Leger, on Cantley Common, Doncaster on September 24, 1776, a total of 42 fillies have won. However, since the St. Leger returned to Town Moor following World War II, just seven fillies – namely Meld (1955), Cantelo (1959), Dunfermline (1977), Sun Princess (1983), Oh So Sharp (1985), User Friendly (1992) and Simple Verse (2015) – have been victorious. The last named was unusual insofar as she did not contest the Oaks, run over a mile and half at Epsom in late May or early June, whereas the other six fillies all did, and all bar Cantelo won the second fillies' Classic.

Owned by Qatar Racing Limited, trained by Ralph Beckett, in Kimpton, Hampshire and ridden, for most of her three-year-old campaign, by Andrea Atzeni, Simple Verse was unraced as a juvenile, but made the transition from handicaps to Pattern level when winning the Group 3 Lilly Langtry Stakes at Goodwood in July, 2015, on the sixth career start. She did not race again until the St. Leger, for which she was supplemented, at a cost of £50,000.

At Doncaster, she was sent off 8/1 fourth choice of the seven runners and won by a head in a driving finish, only to be disqualified for causing repeated interference to the eventual runner-up Bondi Beach, the 2/1 joint favourite, trained by Aidan O'Brien. However, her connections appealed the decision and, 11 days after the race, Simple Verse was reinstated by a British Horseracing Authority (BHA) panel.

Which came first, the 2,000 Guineas, the Derby or the St. Leger?

The 2,000 Guineas, the Derby and the St. Leger are the three British Classic races open to three-year-old horses of both sexes – the other two, the 1,000 Guineas and the Oaks, are restricted to three-year-old fillies – and, as such, constitute the so-called 'Triple Crown'.

The St. Leger, run over an extended mile and three-quarters on Town Moor, Doncaster in September, is the oldest of the trio, having been established, as an unnamed sweepstakes over two miles, on nearby Cantley Common on September 24, 1776. The inaugural winner was an unnnamed filly owned by Charles Watson-Wentworth, Second Marquis of Rockingham, later named Allabaculia. Two years later, the race was transferred to its present location and, at the suggestion of the Second Marquis, named in honour of its founder, Lieutenant General Anthony St. Leger.

The Derby followed four years later, with the inaugural running taking place on May 4, 1780, albeit over the last mile of the old 'orbicular' course at Epsom, rather than the current mile and a half. The race was co-founded by Edward Smith-Stanley, Twelfth Earl of Derby and Sir Charles Bunbury and named after the former as the result of a (probably apocryphal) toss of a coin. The inaugural winner was the hitherto unbeaten Florizel colt Diomed, owned by Bunbury.

Last, but by no means least, came the 2,000 Guineas, which was first run over a mile on the Rowley Mile Course at Newmarket on April 18, 1809, and has continued, almost without exception, ever since. The race was established by the Jockey Club, under the auspices of senior steward Sir Charles Bunbury – as was the 1,000 Guineas, five years later – and the inaugural winner was the odds-on favourite, Wizard, trained locally by Thomas Perren.