In early 1899 the Waverley District Cricket Club played its most important game since its entry into the Sydney grade competition in 1894/95.
The match, against the strong Paddington club, took place on 4 February and 11th February at Waverley Oval. Both clubs boasted test players including Victor Trumper, Monty Noble and Jim “Stumper” Kelly for Paddington and Syd Gregory, Frank Iredale and Sep Carter for the home side. There were also several current first class players in both teams. It was expected to be a match of the highest calibre.
The winner of this match was tipped to go on to win the premiership. Waverley had twice been runner up in the competition and expectations were high this would be the club’s breakthrough season.