Bred in England by Björn Nielsen she showed very promising form as a juvenile in 2003, winning her first two starts before finishing third in the Fillies' Mile.
[2] Punctilious's dam Robertet was a high-class staying racemare who recorded her biggest win in the Grand Prix de Deauville as a four-year-old in 1990.
[4] In November 2002, Punctilious was offered for sale at Tattersalls but was retained by her owner when the bidding failed to reach the reserve price of 190,000 guineas.
On her debut she started favourite for a six-runner maiden race over seven furlongs at Yarmouth Racecourse on 3 July and won by two lengths despite pulling hard against Robinson's attempts to restrain her in the early stages.
[11][12] On 4 June Punctilious was one of seven fillies to contest the 226th running of the Oaks at Epsom Downs Racecourse and was ridden by Dettori who opted to ride her in preference to Sundrop who had finished runner-up in the 1000 Guineas.
Starting the 5/1 third favourite, she took the lead in the straight but was overtaken approaching the final furlong and beaten a length into second place by Ouija Board, with Hazarista taking third ahead of All Too Beautiful.
Racing on soft ground, she led until half way but tired in the straight and finished fourth of the eight runners, more than twenty lengths behind the winner Quiff.
After racing in fifth place she took the lead in the straight but was overtaken in the closing stages and beaten half a length by the Bobby Frankel-trained four-year-old Commercante.
[15] Punctilious began her third season in an exceptionally strong renewal of the Group Three Brigadier Gerard Stakes over ten furlongs at Sandown Park Racecourse on 31 May and finished last of the five runners behind New Morning, North Light, Mubtaker and Grand Passion.
The Australian Kerrin McEvoy took over from Dettori when the filly started 5/2 favourite for the Lancashire Oaks at Haydock Park on 2 July and finished seventh of the eight runners behind Playful Act.
Starting the 15/8 favourite, she was held up by McEvoy towards the rear of the eight-runner field before taking the lead in the last quarter mile and winning by two lengths from the three-year-old Natalie Jane.
The other runners included Iota (Preis der Diana) from Germany, Dash To The Top (Hoppings Stakes), Lune d'Or (Premio Lydia Tesio) and Hazarista.