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Many would place the 2005 Super Bowl loss of the Eagles as the most disappointing moment in Eagles history, but I would not. The Eagles were overall underdogs in this contest, so it does not deserve the top spot on this list, in my opinion.
Nevertheless, it was incredibly disappointing and a game the Eagles should have won.
The Eagles got off to an incredible start against the New England Patriots, and Tom Brady and the Patriots were playing surprisingly poorly in the first half. Then the Eagles squandered opportunities to score early and build an insurmountable lead when they had the chance. McNabb threw a red-zone interception and the Eagles offense stalled following a fumble by Brady that could have granted the Eagles good field position. The Eagles led at halftime 7-0, but in reality should have been up by at least 13-0, if not 21-0.
Then Brady got hot, and the Eagles pass rush could not get to him or rattle him. On the other hand, the Eagles O-line struggled and McNabb was pressured all game.
Regardless, the Eagles found themselves in the fourth quarter with the ball and the score 24-14, in position to mount a comeback. However, with 5:40 left to play, the Eagles oddly ran a game plan that used up 3:52 of the clock and cut the deficit to 24-21, but with only 1:55 remaining. New England ran out the clock and gave the Eagles the ball with 46 seconds left, and the Eagles failed to rally and win the game.
The Eagles defense failed to play up to its expectations, and the Eagles coaching staff failed to call more aggressive plays to give the Eagles the best chance to win at the end of the game.
The loss overall represented a huge failed opportunity and the Eagles failed to deliver a championship despite having one of their best chances in franchise history to do so.