Ottawa Hockey Club & Senators · trainer and coach
Public domain, via Wikimedia Commons
Pete Green won ten Stanley Cups with Ottawa — four as the team's trainer during the 1900s and six as head coach, including the NHL-era Senators champions of 1920, 1921 and 1922.
Pete Green's career spanned the birth of professional hockey. He began with the Ottawa Hockey Club as a trainer, sharing in four early Stanley Cup wins, then became head coach in 1908.
As coach he added six more Cups, including a dominant run with the NHL's Ottawa Senators, who won the Stanley Cup in 1920, 1921 and 1922. Ten championships in one city is a haul that puts this Pete Green among the most successful figures of hockey's founding era.
Sources: Pete Green (ice hockey), Wikipedia · Hockey-Reference