Winifreda was a "great, rangey" bay mare with "rare shoulders and depth"[2] bred in England by Sir Daniel Cooper.

As a broodmare she also produced St Cecilia, the female-line ancestor of the Melbourne Cup winners Backwood, Piping Lane and Tawrrific.

[6] Winifreda made her first and only appearance of 1899 in the Richmond Stakes over six furlongs at Goodwood Racecourse in July, in which she was ridden by Walter Bradford and started 7/4[7] joint-favourite in a four-runner field.

[8] On 4 May Winifreda started the 11/2 third choice in the betting in a ten-runner field for the 87th running of the 1000 Guineas over the Rowley Mile at Newmarket Racecourse.

[11] On 13 June the filly was dropped back in distance for the Coronation Stakes over one mile at Royal Ascot in which she carried top weight of 129 pounds.

After being restrained by her rider Thomas Weldon in the early stages she produced a strong finish and dead-heated for first place with Sainte Nitouche following a "sharp battle" in the final strides.