2002–2004: early career

On his racecourse debut Court Masterpiece finished sixth in a seven furlong maiden race at Ascot Racecourse on 26 July 2002. On his only other start of the season he started 5/2 second favourite for the Convivial Maiden Stakes at York Racecourse in August and finished strongly to win by a short head from the Barry Hills-trained Arctic Burst.^[6] The photo-finish was so close that several of Arctic Burst's supporters attempted to confront the racecourse judge and harangued a Jockey Club spokesman, whilst Hills considered an appeal.^[7]

After finishing fourth at Newbury on his debut as a three-year-old, Court Masterpiece finished second in a handicap race at Epsom and third in the Britannia Stakes at Royal Ascot before finishing unplaced in the Bunbury Cup in July. On 2 August he was moved up to Listed class for the Thoroughbred Stakes over one mile at Goodwood in which he was ridden by Johnny Murtagh and started the 5/1 third favourite behind the Craven Stakes winner Hurricane Alan and the Michael Stoute-trained Laidlow. After being restrained towards the rear of the field in the early stages he took the lead inside the final furlong and won by a length from Hurricane Alan.^[8]

Court Masterpiece was off the course for more than nine months before returning to finish third at Goodwood in May 2004. He went on to finish fifth in the John of Gaunt Stakes, fourth behind Vortex in the Criterion Stakes and second in the Bunbury Cup. On 24 July, the colt was assigned a weight of 128 pounds for the International Stakes, a valuable handicap race over seven furlongs at Ascot. He was ridden by Kieren Fallon and started 7/1 second favourite in a twenty-one runner field with Vortex (carrying 121) heading the market on 4/1. He was held up by Fallon in the first quarter mile before moving up to track the leaders approaching the final furlong. He took the lead 150 yards from the finish and won by a neck from Polar Way.^[9] He was moved back to Group races for his last three starts of the season, finishing fourth in Celebration Mile, third in the Park Stakes and sixth in the Supreme Stakes.

2005: five-year-old season

Court Masterpiece began his fourth season by finishing fourth under top weight of 136 pounds in the Victoria Cup and then finished second when 8/13 favourite for a minor event at Leicester Racecourse. On 3 June the horse started 13/8 favourite for the Listed On The House Stakes over one mile at Goodwood. Ridden by Fallon, he took the lead approaching the final furlong and drew away to win "very easily" by nine lengths from the three-year-old Elliots World.^[10]

Three weeks after his win at Goodwood, Court Masterpiece was beaten a short head by his old rival Vortex in the Criterion Stakes, before finishing a neck behind Autumn Glory in the Silver Trophy Stakes with Vortex in third. On 26 July, the horse faced Autumn Glory and Vortex again in the Group Two Betfair Cup over seven furlongs at Goodwood in which he was ridden for the first time by Philip Robinson. Starting at odds of 4/1, he tracked the leaders, overtook the four-year-old Jack Sullivan inside the final furlong and held off the renewed challenge of his rival to win by a short head with a gap of three lengths back to Majors Cast in third.^[11] After the race Robinson said "I'm thrilled for the horse, he's been placed in so many group races and finally managed to win one".^[12]

On 28 August Court Masterpiece finished third behind Chic and Majors Cast in the Celebration Mile and then ran third again, beaten a short head and three lengths by Iffraaj and Sleeping Indian when carrying top weight of 130 pounds in the Park Stakes at Doncaster eleven days later. On 5 October, on his twenty-fourth start, the horse contested his first Group One race when he was sent to France for the Prix de la Forêt over 1400 metres at Longchamp Racecourse. The British-trained sprinter Somnus started favourite ahead of Iffraaj and the Irish four-year-old Caradak (Desmond Stakes, Minstrel Stakes), with Court Masterpiece next in the betting on 8/1. The other runners included Coupe de Champe (Prix de la Porte Maillot, Prix du Pin) and Toupie (Prix d'Arenberg). Ridden by the French jockey Gerald Mosse he was held up in the early stages and reached the final turn before making rapid progress down the centre of the Longchamp straight. He caught Caradak in the final strides and won by a head with Mirabilis a short neck away in third.^[13][14]

On his final appearance of the season, Court Masterpiece started at odds of 14/1 for the Hong Kong Mile at Sha Tin Racecourse on 11 December and finished fifth of the thirteen runners behind the Japanese four-year-old Hat Trick.

2006: six-year-old season

Following the death of Maktoum Al Maktoum in January 2006 Court Masterpiece raced in the ownership of the Gainsborough Stud. He began 2006 in the United Arab Emirates where he finished sixth in the Godolphin Mile in March. On his return to Europe he contested the Group One Lockinge Stakes at Newbury on 20 May and finished third behind Peeress and Majors Cast. At Royal Ascot in June he started third favourite behind Peeress and Proclamation for the Queen Anne Stakes, which also attracted Vortex and the Aidan O'Brien-trained Ad Valorem. Ridden by Jamie Spencer, he was hampered when making a strong challenge in the straight and finished second, one and a half lengths behind Ad Valorem. Spencer felt that the interference had cost his mount the race, but the racecourse stewards left the result unchanged.^[15]

On 2 August, Court Masterpiece was one of seven horses to contest the Group One Sussex Stakes over one mile at Goodwood in which he was ridden by Jimmy Fortune. Araafa, a three-year-old colt who had won the Irish 2000 Guineas and the St James's Palace Stakes on his last two starts was made favourite ahead of the outstanding racemare Soviet Song and the Summer Mile Stakes winner Echo of Light with Court Masterpiece fourth choice on 15/2. The other runners were Aussie Rules (Poule d'Essai des Poulains), Rob Roy (Joel Stakes) and the 100/1 outsider Vanderlin (Play the King Stakes). Fortune held the horse in fifth place as Echo of Light set the pace from Araafa before making progress approaching the last quarter mile. Araafa took the lead but Fortune switched Court Masterpiece to the inside, overtook the favourite a furlong out and opened up clear advantage. He won by two lengths from Soviet Song, with Rob Roy half a length away in third place.^[16] Commenting on the horse's fourth win at the track, Ed Dunlop said "He was very unlucky at Ascot when nearly knocked over, but that's history and he's now one of the best milers in Europe"^[15] and added "he's very good round here, and he's won like a very good horse. I'm very pleased for him. I would like to take him to America for the Breeders' Cup Mile, he would be a companion for Ouija Board (horse), but we'll take him home and have a think".^[17]

On his next appearance, Court Masterpiece finished third to George Washington and Araafa in the Queen Elizabeth II Stakes at Ascot on 22 September. In late autumn he was sent to race in Japan but failed to reproduce his best European form, finishing unplaced in the Mile Championship and the Hanshin Cup.

2007–2009: later career

In 2007, Court Masterpiece entered the ownership of Princess Haya of Jordan, the wife of Sheikh Mohammed and was trained first by Ismail Mohammed and then by Saeed bin Suroor. He raced twice in Dubai without success, finishing eighth in the Al Fahidi Fort in February and fifth behind Spring At Last in the Godolphin Mile.

After an initial failure at stud, Court Masterpiece was acquired by the insurance company QBE (Europe) before entering the ownership of Maxilead Limited. He was returned to the track in 2009 when trained by John Quinn at Settrington in Yorkshire. He failed to win in six races, ending his career by finishing fourth in a claiming race at Musselburgh Racecourse in September.