1900: two-year-old season Volodyovski was beaten in his first two races, including an unplaced effort at
Kempton on 2 June, but was nevertheless sent to run against top class opposition at
Royal Ascot in June. Starting at odds of 100/7, he finished strongly to take second place behind Good Morning in the
Coventry Stakes and then won the Windsor Castle Stakes. Volodyovski then won his next three races, taking the Stud Produce Stakes at
Newmarket, showing "great resolution" to beat Princess Melton by a neck and two Rous Memorial Stakes at
Goodwood (by three lengths "drawing away") and Newmarket ("in a canter"). At
Kempton he finished second in the Imperial Produce Stakes, in which he was attempting to give thirteen
pounds to the filly Aïda, who went on to win the
1000 Guineas. On his final race of the season he won the Great Sapling Stakes at
Sandown. Volodyovski went into the winter break as 9/2 favourite for the following year's Derby. In December, Lord William Beresford died, and the ownership of Volodyovski became a matter of dispute: Beresford's widow argued that she should inherit the lease of the colt, whilst Lady Meux wished the arrangement to be terminated. In early 1901, the ownership of Volodyovski was decided in court where the Judge ruled that the lease was invalidated by Beresford's death. Lady Meux promptly leased the colt to the wealthy American businessman,
William Collins Whitney.
1901: three-year-old season Volodyovski had not been entered in the
2000 Guineas and his early preparation was not hurried by Huggins. He finished third, looking "palpably unfit" on his seasonal debut in a Biennial Stakes at Newmarket in April. By this time he had acquired the Anglicized nickname "Bottle o' Whisky" from
bookmakers and members of the public who struggled with the pronunciation of the colt's name. At Epsom on 5 June, Volodyovski started the
5/2 favourite for the Derby in a field of twenty-five runners. Ridden by the American jockey
Lester Reiff, Volodyovski was held up in the early stages and was not among the front-runners as the outsider Olympian led the field into the straight. In the final quarter mile Reiff made his challenge and Volodyovski "dashed to the front". In the closing stages he was challenged by
William the Third but after briefly looking to be in trouble when he was startled by the noise of the crowd, he pulled away before being eased down in the final strides to win by three quarters of a length. The winning time of 2:40.8 was a new race record. Following his win, William Whitney offered to buy a drink (a "Huggins Punch") for every spectator at
Gravesend Race Track, which proved expensive as his offer was taken up by 8,000 patrons. Whitney donated his winnings from the Volodyovski's Derby win to the
Jockey Club benevolent fund. In his first start after winning the Derby, Volodyovski faced William the Third again in the Lennox Stakes at
Hurst Park Racecourse on 24 August. He was beaten a head by the Derby runner-up, to whom he was conceding three pounds. In the
St Leger at
Doncaster in September Volodyovski finished second, beaten a head by Doricles in a rough and controversial race. It appeared that several of the English jockeys had connived to prevent Reiff from winning the race, but an objection lodged Volodyovski's connections was rejected by the stewards. In October, Volodyovski won the Sandown Foal Stakes and then ran against older horses for the first time in the Kempton Park Stakes. He proved to be the best of the three-year-olds, beating Doricles and William the Third, but finished third behind the four-year-olds Epsom Lad and Santoi.
1902: four-year-old season Volodyovski was kept in training as a four-year-old in 1901, but failed to reproduce his earlier form, losing all eleven of his races. He began his season by finishing third in the
Lincolnshire Handicap. He finished unplaced in the Great Jubilee Handicap at
Kempton and then finished second to Osbech in the
Coronation Cup, by which time he had become a confirmed
roarer. In September Volodyovski finished second in the Prince Edward Handicap, conceding 36 pounds to the winner and was the beaten favourite in the Duke of York Stakes at Kempton in October. ==Assessment==