The bay filly, Wakeful was foaled by breeder W.R. Wilson in 1896 at Geelong, and was by the outstanding racehorse and sire, Trenton. One of the best Australian sires of his time, Trenton was exported to England at 15 and made a big contribution to world breeding as the sire of the second dam of breedshaper, Gainsborough. Insomnia, a daughter of noted Australian racehorse Robinson Crusoe, an 11 time winner from 19 starts was her dam. Trenton’s sire was the English horse Musket that did follow the pattern of leaving England for the Southern Hemisphere, arriving in New Zealand in 1878. Insomnia's pedigree contained mostly good old colonial bloodlines that had proved their worth in Australian racing and breeding. She was offered at the St Aubins stud dispersal sale and was purchased by Leslie Macdonald for the bargain price of 310 guineas.

Wakeful did not commence racing until she was four because of shin soreness. She began her racing career during the 1900-01 racing season. At her third start she won the VATC Oakleigh Plate, and followed that by winning the VRC Newmarket Handicap and then the Doncaster Handicap in a race record time of 1:39.75. Her last race that season was in April of 1901 with a third-place finish in the Sydney Cup where she jumped from 1600m to 3200m in distance.

Taken to Sydney in 1902, Wakeful won all her four starts including the Sydney Cup carrying the impost of 9 stone 7 pounds (60 kg), and ran a race record. Wakeful then went on to win races such as the AJC Plate and VRC Champion Stakes at three miles. At her last start she ran second in the 1903 VRC Melbourne Cup carrying the huge weight for a mare of 10 stone (64 kg) which was 13 pounds over weight for age and conceded the winner Lord Cardigan 3st 6lb (22 kg). Previously no mare had carried more than 9st 7lb and none of them finished in the first six. In all she had 44 starts, winning 25 races, was second 12 times and third 4 times

Fifteen years after concluding her racing career, Wakeful produced the mighty Night Watch, winner of the 1918 Melbourne Cup. Two of her other offspring that fared well as gallopers were Blairgour, winner of the Memsie Stakes and the Oakleigh Plate, and Baverstock, the sire of David, a 1923 Sydney Cup winner. It would be an exaggeration to claim that Wakeful is the greatest mare in Australian racing history, considering the elite accomplishments of Makybe Diva, Black Caviar, and Sunline. However, it is reasonable to consider her as one of the all-time greats within the formative years of Australian racing. Notably, her racing performance is comparable to that of great stallions of the era.

RACE RECORD - 44: 25-12-4
EARNINGS - £16,690

Oakleigh Plate (1901)
Newmarket Handicap (1901)
Doncaster Handicap (1901)
Caulfield Stakes (1901, 1902)
Melbourne Stakes (1901, 1902, 1903)
St George Stakes (1902)
Essendon Stakes (1902, 1903)
VRC All Aged Stakes (1902)
AJC Autumn Stakes (1902)
Sydney Cup (1902)
AJC All Aged Stakes (1902)
AJC Plate (1902)
AJC Spring Stakes (1902)
AJC Craven Plate (1902)
Randwick Plate (1902)
C.B.Fisher Plate (1902)
October Stakes (1903)
VRC Champion Stakes (1903)