Oscar Whisky was a bay gelding with a white star and snip bred by Stephanie Hanly at Grange Hill Stud in Nenagh, County Tipperary.
Starting the 8/15 favourite, he took the lead two furlongs from the finish and won by four lengths from Midnight Prayer, with the future Champion Hurdle winner Rock On Ruby in fourth place.
Oscar Whisky was prepared for the 2010 Cheltenham Festival with a very easy[11] win in a novice hurdle at Sandown, beating ten opponents at odds of 4/11.
At Cheltenham on 16 March 2010, Oscar Whisky started the 11/1 third favourite for the Grade I Supreme Novices' Hurdle and finished fourth of the eighteen runners behind Menorah, Get Me Out of Here and Dunguib.
In the closing stages Oscar Whisky held off a strong challenge from Thousand Stars to win by a neck, with a gap of ten lengths back to the outsider Salden Licht in third place.
[15] On his first appearance of the 2011/2012 National Hunt season, Oscar Whisky was made 5/6 favourite for the Grade II Ascot Hurdle in November, but fell heavily when challenging Overturn for the lead at the last obstacle.
[20] Oscar Whisky began the next season in the Ascot Hurdle and won easily by eight lengths from Raya Star, having led from the start.
[21] Only two horses appeared to oppose him in the Relkeel Hurdle, and he had no difficulty repeating his 2011 success in the race, leading all the way and finishing nineteen lengths clear of Crack Away Jack.
Although he stayed on well in the closing stages, Oscar Whisky failed to overhaul the leader Reve de Sivola and was beaten a neck.
In April, he attempted to win his third consecutive Aintree Hurdle in which he was ridden by A. P. McCoy, with Geraghty partnering the Henderson stables other runner Grandouet.
He made his debut over the larger obstacles at Cheltenham on 15 November when he stated the 4/6 favourite but was beaten a neck by the Jonjo O'Neill-trained six-year-old Taquin de Seuil in a race which was run at very slow pace and resulted in a sprint finish.
[26] Commenting on what was described as a rather disappointing performance, Henderson suggested that the horse had not been suited by the soft ground and added, "He's a stuffy devil, that's why he had to have a run.
[27] On 13 March, Oscar Whisky started 9/2 second favourite for the Grade I JLT Novices' Chase at the Cheltenham Festival but fell at the first fence.
At Aintree a month later he started 7/4 favourite for the Grade I Manifesto Novices' Chase and finished second, beaten one and a half lengths by the French-bred six-year-old Uxizandre.
On his first appearance of the 2014/2015 National Hunt season Oscar Whisky was assigned top weight of 166 pounds in the Paddy Power Gold Cup over two and a half miles at Cheltenham on 15 November.
Starting at odds of 6/1 in an eighteen-runner field he recovered from a bump at the third last and finished well to take fourth place, two and a quarter lengths behind the winner Cead du Berlais.