In 1920, Darragh became the first player in the NHL era to score three game-winning goals in a Stanley Cup Finals series - a mark that has since been tied, but never surpassed.

They finally came to terms at the eleventh hour and two—they even missed part of the first game, which the Senators ended up losing 7-4 to the Montreal Canadiens.

[2] Darragh retired for a second time after the 1923–24 season and died a few months later due to peritonitis, which was the result of a ruptured appendix.

Although without any background in organized junior hockey, Jack Darragh was a good skater and had speed to burn to go along with much grit and determination, playing a fast and strong game on the forward line.

[10] While considered a clean and gentlemanly player, Darragh still carried a fair amount of pluck to his game, and during the 1913–14 NHA season he led the Ottawa Senators with 69 penalty minutes.

According to the newspaper Darragh was a "beautiful specimen of an athlete and his weight, coupled with terrific speed and magnificent stickhandling, made him a terror to opposing teams.

[12] One such instance happened in the 1920 Stanley Cup Finals against the Seattle Metropolitans where the fifth and deciding game between the two teams stood at 1-1 after two periods.

At his residence on Java Avenue in Ottawa, just prior to his death, he had also built an adjoining clay tennis court to train on.