Which is the oldest regulated horse race in the world?

It stands to reason that the oldest regulated horse race in the world should have originated in one of the oldest established centres for horse racing in the world. Doncaster Racecourse is not the oldest racecourse in the world – that distinction belongs to Chester Racecourse, established in 1539 – but a racecourse is shown in the vicinity of Doncaster, on Wheatley Moor, on a map dating from 1595.

The oldest regulated horse race is in the world, in fact, the Doncaster Cup, which was established, as the Doncaster Gold Cup, in 1766, a decade before the oldest British Classic, the St. Leger Stakes, also run at Doncaster Racecourse. Nowadays, the Doncaster Cup is a Group Two contest run over two miles and two furlongs and, along with the Gold Cup at Ascot and the Goodwood Cup, constitutes part of the so-called Stayers’ Triple Crown. However, the Doncaster Gold Cup was originally run over four miles, on Cantley Common, before being transferred to its current home, on Town Moor, ten years later.

Has any jockey ever won the Lincoln and the Grand National?

The Lincoln Handicap, run over a mile at Doncaster, traditionally marks the start of the Flat season ‘proper’ in Britain and is usually staged a week or two before the Grand National. Collectively, the two races constitute what is known as the ‘Spring Double’ but, granted the distinct demands of the disciplines in which they take place – not least the weights carried by the horses – few jockeys have ridden in, never mind won, both.

Remarkably, the one and only jockey to win both races was David Dick, who is probably best remembered as the jockey of E.S.B., the horse that profited from the inexplicable fall of Devon Loch, just yards from the winning post, in the Grand National in 1956. By that stage of his career, Dick stood 6’ tall and was, at least in theory, too big to a jockey of any description. Nevertheless, as a lithe 17-year-old, in 1941, Dick had also ridden Gloaming to win the Lincolnshire Handicap at Lincoln, which subsequently became the Lincoln Handicap at Doncaster.

Has any horse ever won all five British Classics?

Of the five British Classics, two of them – that is, the 1,000 Guineas and the Oaks – are restricted to three-year-old thoroughbred fillies, so it is impossible for a colt to win more than three. That said, a total of fifteen colts have won the 2,000 Guineas, the Derby and the St. Leger, a.k.a. the ‘Triple Crown’, while nine fillies have won the 1,000 Guineas, the Oaks and the St. Leger, a.k.a. the ‘Fillies’ Triple Crown’. Remarkably, though, two of those fillies not only ran in, but won, the 2,000 Guineas, taking their tally to four English Classics.

In 1868, Formosa, trained by Henry Woolcott, dead-heated with the colt Moslem in the 2,000 Guineas, before easily winning the 1,000 Guineas, over the same course and distance, two days later. She subsequently won the Oaks, by 10 lengths and, despite being beaten, twice, at Royal Ascot, was sent off joint-favourite for the St. Leger at Doncaster, which she duly won by 2 lengths under just hands-and-heels riding.

In 1902, Sceptre, owned and trained by Robert Sievier, started her three-year-old by being narrowly beaten, under 6st 7lb, in the Lincolnshire Handicap, but went on to win the 2,000 Guineas and the 1,000 Guineas, again within two days. She was arguably unlucky not to win the Derby, finishing fourth after missing three days’ work with a bruised foot, but returned to winning ways when hacking up in the Oaks two days later. Subsequently, she ran in the Grand Prix de Paris, twice at Royal Ascot and twice at Glorious Goodwood but, come the autumn, still managed to beat Rising Glass, who had finished second in the Derby, in the St. Leger. In so doing, she became the first and, so far, only horse to win four British Classics outright.

What happened to Shergar?

Having won the Derby by 10 lengths – still the widest winning margin in the history of the race – in 1981, Shergar was, for a time, the most celebrated racehorse in the world. Following his last race, in the St. Leger Stakes at Doncaster, later that year, he was retired to Ballymany Stud, in Co. Kildare, Ireland, where he was syndicated for £10 million.

However, less than two years later, on a murky night in February, 1983, Shergar was abducted by a gang of masked gunmen, believed to belong to the Irish Republic Army (IRA), and never seen again. Ransom negotiations – conducted, bizarrely, by British horse racing journalist Derek Thompson – followed, but ended abruptly with an anonymous, but coded, message that Shergar had died ‘in an accident’.

Exactly what happened to Shergar remains an abiding mystery. He may well have died, as suggested by more than one former IRA member, in a hail of machine gun bullets in a stable at a remote farm near the town of Ballinamore in Co. Leitrim – former ‘bandit country’ – near the border with Northern Ireland, after becoming distressed by his new surroundings. However, the IRA has never officially claimed responsibility for his disappearance, his kidnappers have never been officially identified and his remains have never been found.