5. Losing Game 7 to the hated Maple Leafs in 2002
The Senators' arch rival in the NHL are the Toronto Maple Leafs. The Battle of Ontario intensifies more with every game. The two teams have met four times in the playoffs with the result being the same with the Maple Leafs eliminating the Senators, but no playoff series loss was worse against the Maple Leafs than in 2002.
After the Senators defeated the Flyers in the first round of the 2002 playoffs, the Senators had a date with the Maple Leafs in round two. Even without having home ice advantage, the Senators believed they can knock off the Maple Leafs.
The series immediately started in Ottawa's favor when Ottawa won 5-0 in Game 1. The Maple Leafs won a hard fought triple overtime game in Game 2 to even the series. For the next two games in Ottawa, each team won a one-goal game to make the series tied at two going back to Toronto for Game 5.
The Senators put themselves in position to knock off their arch rival in round two after winning Game 5 by a final of 4-2. With the Ottawa crowd buzzing for Game 6, the Senators suffered a heartbreaking 4-3 loss in Game 6, and at one point held an early 2-0 lead. The Senators were shutout 3-0 in Game 7 and were eliminated from playing in the 2002 Eastern Conference Finals against the Carolina Hurricanes.
Losing Game 7 to your arch rival will always be a heartbreaking and painful moment, and 2002 will always live on in the Senators-Maple Leafs rivalry.