[7] Shortly after buying Speciosa, Sly engaged the County Limerick-born jockey Michael "Micky" Fenton to ride her in a training gallop.
Fenton sent the filly to the front from the start, and she maintained her lead to the finish, winning by a neck from Violette with the future Sun Chariot Stakes winner Spinning Queen in sixth.
[11] During the winter of 2005/2006, Speciosa's owners turned down several large offers to buy the filly: Pam Sly was over-ruled by her partners after advising them to accept a £1,000,000 bid.
She led throughout the race and prevailed by a length from Spinning Queen, although she again showed a tendency to hang left inside the final furlong.
In the final quarter mile, many of the runners began to tire on the soft ground, but Speciosa stayed on under pressure, and although she yet again drifted to the left, she won by two lengths from Confidential Lady with Nasheej in third.
Pam Sly described the win as being "for all the little people" and the success of a small stable was contrasted with those achieved by the major international racing organisations such as Coolmore/Ballydoyle and Godolphin.
[12] Pam Sly paid a £20,000 supplementary fee to run Speciosa in The Oaks a month later, as the filly had not been one of the original entries for the mile and a half race.
[15] Starting at odds of 5/1, Speciosa led until the final quarter mile before being overtaken and finishing fourth to the Irish-trained filly Alexandrova.
She began her season by racing against colts in the Earl of Sefton Stakes and produced a promising performance[16] to finish second to the 2007 World Champion Manduro.