After showing promise in National Hunt Flat races in Ireland, he recorded his first major success when winning the Ballymore Properties Novices' Hurdle at the 2008 Cheltenham Festival.

Fiveforthree is a grey horse bred at the Rusellstown stud near Mullingar in County Westmeath by Peter and Ann Downes.

[4] Three years later, Fiveforthree, now a three-year-old gelding, was sent to the Doncaster Bloodstock Sale in England but was not sold as he failed to reach his reserve price of 24,000 guineas.

[8] On his final appearance of the season at Fairyhouse in April he started 6/4 favourite but finished third behind Sizing Africa and Mick The Man.

After a ten-month break, (he had injured his ribs when "rolling in the paddock")[9] Fiveforthree returned to compete novice hurdle races, making his first appearance over obstacles at Fairyhouse on 13 February 2008.

He was the 7/1 fourth choice in the betting behind the former flat runners Aigle d'Or and Group Captain and the Deloitte Novice Hurdle winner Forpadydeplasterer.

After another long break, Fiveforthree returned in a two-mile hurdle at Wexford Racecourse on 17 March 2009 and won by seven lengths at odds of 4/9.

He visited England for the third time on 4 April when he contested the Grade I Aintree Hurdle over two and a half miles at the Grand National meeting.

Fiveforthree was off the racecourse for two years before returning for the Coral Cup, a handicap hurdle over two miles five furlongs at the 2013 Cheltenham Festival.

In April he attempted to repeat his 2009 success in the World Series Hurdle at Punchestown but finished fifth of the six runners behind the mare Quevega.