It is reasonable to assert that Wakeful was the greatest mare ever to have raced in Australia. She did not start racing until four years old, continuing until she was seven. It was her versatility that made her exceptional. The first wins were in those sprint classics in 1901, the Oakleigh Plate at Caulfield and the Newmarket Handicap at Flemington, followed directly by the Doncaster Handicap at Randwick. In the spring she returned to win the Caulfield Stakes, then was second in Caulfield Cup and next won what was called the Melbourne Stakes on Derby Day. In her first try at a Melbourne Cup she finished fifth to Revenue.
The next autumn her seven victories included the 1902 Sydney Cup which she won, smashing the course record while carrying 61.2 kilograms. Her ten wins at age six included a Champion Race at Flemington over a marathon 3 miles (4828 metres). At seven she was handicapped to carry top weight of 10 stone (63.4 kilograms) in the 1903 Melbourne Cup. Her jockey, Fred Dunn, had won the Cup on Revenue in 1901 but miscalculated this time by taking Wakeful to the front half a mile from home. The three-year-old Lord Cardigan with boy jockey Noel Godby carried 43.7 kg – yes! –20 kilograms less on his back. Even so, he could only just catch Wakeful in the shadows of the post. The sentimental favourite lost. People wept openly in the stands and cheered her back to the saddling yard as a champion.
The postscript to the Wakeful story is that she also triumphed as a broodmare. She herself was a daughter of Trenton (twice placed in Melbourne Cups in the mid-1880s). Her dam, appropriately named, was Insomnia, daughter of Nightmare. Wakeful gave birth to ten foals. Nine raced and six were winners – including Blairgour who won an Oakleigh Plate, and Night Watch who won the 1918 Melbourne Cup. Wakeful is the only Cup-winning mare to produce a Cup winner.