The 1926–27Ottawa Senators season was the club's tenth season of play in the NHL, 42nd overall. The Senators would win the Stanley Cup for the fourth time in seven years, and eleventh overall including the pre-NHL years.
Prior to the start of the season, the Senators relieved head coach Alex Currie from his duties. General Manager Dave Gill would step behind the bench and become the head coach. Buck Boucher would take over the team captaincy from Cy Denneny.
The league would expand by three teams, as the Chicago Black Hawks, Detroit Cougars and New York Rangers would all join the league to make it a ten-team league. The NHL also would divide the ten teams into two divisions, and the Senators found themselves in the Canadian Division. This was also the first season that the Stanley Cup was awarded to the champion of the NHL.
The Senators would win 30 games and earn 64 points, both the highest in the NHL and capture the Prince of Wales Trophy, win the Canadian Division title, and earn a bye in the opening round of the playoffs. Also,
Denneny would go on to lead the club once again offensively, scoring 17 goals and 23 points, while Hooley Smith would have a team record 125 penalty minutes. Alec Connell would lead the NHL in wins (30) and be among the league leaders in GAA (1.49) and shutouts (13).
The Montreal Canadiens would defeat their cross town rivals, the Montreal Maroons and face the Senators in a two-game total-goal series, and Ottawa would win it by a score of 5–1, and match up against the Boston Bruins in the Stanley Cup Final.
Ottawa Senators 5, Montreal Canadiens 1
Led by Cy Denneny and Alec Connell, the Senators would win a tough four game series over the Bruins, winning the Stanley Cup for the fourth time in seven years.
Eddie Gerard's name was misspelled when the ring was engraved as F. GERAD (MGR) instead of E. GERARD (MGR)on the 2nd version of the ring created in 1969. The mistake was repeated on the Replica Cup created in 1992–93.