The first organized hockey team in Ottawa was the Ottawa Hockey Club, which was formed in 1884 at the 1884 Montreal Winter Carnival. They would later be dubbed the Generals, because of their war emblem style logo in 1890.

The Generals would help found the first major organized hockey league in Canada called the AHA (Amateur Hockey Association) in 1886. In 1890 they also helped found the OHA (Ontario Hockey Association) and played in both leagues until about 1895/96, where they dropped out of the OHA to concentrate exclusively on the AHA.

In 1893 the Generals barely lost out to the Montreal AAA as champions of the AHA and therefore, just lost out on winning the very first Stanley Cup. Desperate to win a Cup for Lord Stanley (who lived in Ottawa at the time), the Generals faced off against the Montreal AAA on March 22, 1894, in what is considered the first Stanley Cup Finals game ever played.

Ottawa grabbed an early 1-0 lead thanks to Chauncey Kirby's goal, as the Generals dominated thanks mostly to the inspired play by a young Harvey Pulford. However, Montreal stormed back with three straight goals to win 3-1 and retain the Cup.

The Generals would not challenge for the Stanley Cup for ten years as their 1901 CAHL Championship was too late in the year to put a challenge in for the Cup.