[9] Rock On Ruby was then promoted to the highest level at the Cheltenham Festival where he ran in the Grade I Neptune Investment Management Novices' Hurdle over two miles five furlongs.

Rock On Ruby took a slight lead at the second last hurdle and looked the likely winner[12] but after what the Racing Post described as a "thrilling battle",[13] finished second to Binocular, beaten a neck at level weights.

From the start of the race, Rock On Ruby, ridden by Noel Fehily, tracked the leader, Overturn, and then moved up to dispute the lead two hurdles from the finish.

He took a decisive advantage turning into the straight and ran on strongly under pressure, showing what the Daily Telegraph described as "tremendous courage"[14] to win going away by three and three quarter lengths from Overturn, Hurricane Fly, and Binocular.

On 16 December, the gelding ran in his first steeplechase when he started 1/10 favourite for a minor Novice race at Plumpton Racecourse and won "very easily" by four lengths.

[17] Only one horse, the Nicolls-trained Mr Mole appeared to oppose Rock On Ruby when he warmed up for the 2014 Cheltenham Festival in a novice chase at Doncaster on 9 February.

[18] On his first appearance of the new season, Rock On Ruby finished third in the Elite Hurdle at Wincanton on 8 November, conceding thirteen pounds to the winner Purple Bay.

Four weeks later the gelding added a win in the Dornan Engineering Hurdle over the same course and distance, beating Vaniteaux and Cole Harden by two and a half lengths and a neck.

He raced in second before taking the lead at the second last but was badly hampered when Arctic Fire fell at the final hurdle and finished second, thirteen lengths behind Jezki.

He travelled well and looked to be overtaken in the home straight but after a major jumping mistake by one of the threatening rivals, Rock On Ruby managed to find more and extended at the line to win by two and half lengths.

Less than a week later on 27 November, trainer Harry Fry announced that Rock On Ruby has been retired following a tendon injury that he suffered when winning the Ascot Hurdle.