For the Senators, I'd rank it as follows:
The legitimate one:
1. 2003
I think this was the one we thought we had. President's Trophy winners, come back in the series against New Jersey, perfect 4-0 record in OT, tied late in the 3rd in Game 7.
Then Jeff Friesen. I was in the rink for this one, and it's as quiet as it's ever been.
In my opinion, this is the only legitimate one.
I think Ottawa would have won the final much as New Jersey had done.
This was the one that broke Ottawa's collective hearts I think.
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The debatable ones:
2. 2006
This is a tough one because it only would have been possible with Hasek standing on his head (as he had been doing all season) but he was out for the year as of February at the Olympics. Ottawa had played a very loose (and exciting to watch) system all year long, bolstered by the crackdown on obstruction and increased PPs. They scored 10 on Ryan Miller and Buffalo on a night where Alfredsson had 4 goals, Havlat had 4, and Heatley had 2 (10-4 final). They gave up a lot of shots, but Hasek was there.
As it was, we had an inexperienced Ray Emery in net and he gave up 7 in that first game against Buffalo in the 2nd round.
Ottawa's style did not lend itself to tight-checking playoff hockey against a Buffalo squad led by Jay McKee and Mike Grier that blocked every shot and battled in every corner. Add an injured Zdeno Chara to the mix and it just wasn't in the cards. They peaked at the wrong time.
3. 2007
Here's a team that peaked at the right time. Out of the playoffs by Christmas, injuries to Ottawa's top 3 centres, and the team rallied with some late December heroics and tough, two-way hockey.
They rode into the playoffs as the league's hottest team and put Crosby and Malkin, Brodeur and the Devils, and the President's Trophy champs and the previous year's nemesis Sabres out in three straight 5-game series.
The Pizza line was the league's hottest line but it was the commitment to two-way hockey, strong penalty killing and limiting second chances on the part of the opposition that paved the way to the final.
Only to have a 10 day layoff, and then run into the Anaheim Ducks, who were more than happy to play a tough, grinding series after knocking out the Wings in similar fashion. 3 one-goal victories decided in the 3rd period, and the Senators were out in 5.
That Ducks team was strong, with Pronger, Niedermayer and Beauchemin a huge advantage over Volchenkov, Phillips and Redden. Not to mention Perry and Getzlaf as supporting players behind guys like Selanne and MacDonald, and the impressive shutdown line of Pahlsson, Moen and Niedermayer.
Could Ottawa have won that series? A five game series is a short series, but the games themselves were relatively close. Still, it was a tough challenge which is why I stick it on this side of "should have won the Cup". Not to mention, while the Red Wings might have been the slightly better match-up, they were still an extremely fearsome opponent.
Ottawa was a decent team that year, not as good as the 2003 or 2006 teams, but they got hot at the right time, and were already playing playoff hockey near the end of the regular season.
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The non-debatable ones:
4. 2005
To me, this is not debatable.
There was no season.
Assuming the Senators would have come close to the Cup without having played a single game is bizarre.
Sure, we had some guys in their primes, but anything can happen in the course of a season. Injuries? Slumps? Getting cold at the wrong time?
There's no evidence of any kind to go on.