I admit, this list could be changed on Sunday if the Jets fail to beat the Bengals. It would be technically the new year, but it's still this season, so it would have to be on here.
This is a completely subjective list based on how important the game is, how devastating the loss was, and a whole other group of factors that I can't really explain. Just take it for what it is, and if you disagree, send some comments with your choices and relive the heartbreak that has defined being a Jets fan for so long.
10. December 26, 2004. Week 16: Patriots 23, Jets 7
Throughout most of the decade, the Patriots dominated this series, and it's hard to choose just one game to go on here. But the 2004 season summarized this rivalry. The Jets and Pats squared off at 5-0 in week 7 that year, with the Patriots coming out victorious. The Jets had a chance to get revenge in week 16. The Patriots were coming off a loss on Monday night against a bad Dolphins team, which dropped them to 12-2. The Jets were two games behind, but they had a chance to make a statement, but instead, they came out flat, falling behind 23-0 early as the Jets could get little going offensively. The Jets never won more than 10 games in a single season this decade, and this would have given them the chance for more, and it would have been a big moral victory.
9. January 12, 2003. Divisional Round: Raiders 30, Jets 10
Oakland was the Jets' nemesis early in the decade. The Jets had won their last two games by a total of 83-17, but the Raiders didn't let Chad Pennington and the Jets' offense get on track. Did Oakland expose Pennington, as many asserted after the game? Or did his preseason injury in 2003 and the numerous other injuries in the following years derail his career? Nobody knows, but this might have been the best Jets' team of the decade, so ending the season out in Oakland as anticlimactically as it was, was extremely disappointing.
8. December 21, 2008. Week 16: Seahawks 13, Jets 3
The difference between the 2008 and the 2009 Jets is that the 2009 Jets outplayed their opponents in many of their losses. The 2008 Jets simply didn't show up half the time late. This started with a home loss to Denver, but at least the Broncos were a decent team. Losing to San Francisco one week after that was bad, too, but after a miraculous home win against Buffalo, the Jets had a road game against an awful 3-11 Seahawks team that would have given them a huge lift into the playoffs. Seneca Wallace was quarterbacking the Seahawks, yet he outplayed Brett Favre, and the Jets only managed 3 points in the biggest game of their season. Down 10-3 the Jets had one last chance. On a 4th and 2 at their own 20 yardline, Favre threw a deep ball to Laveranues Coles, which went in and out of his hands, a microcosm of the season slipping away right between their fingers.
7. December 20, 2009. Week 15: Falcons 10, Jets 7
2009 has brought us a litany of potential games to go on here. And just when it appeared the Jets couldn't top themselves, they brought us this shot to the gut that led everybody, including the coach, saying the Jets were out of the playoffs. As it turns out, that wasn't at all the case, but the heartbreak after the game was just as real as any of these other games. Gang Green dominated this football game from the start, but they botched three field goals, with the holder, kicker, and long snapper each taking the blame for one. The Jets were in Falcons territory five times but came away with no points, and the #1 ranked defense, which had been stout all game and all season, let Matt Ryan go right down the field on the Jets to set up a 1st and goal. The defense held on the first three plays, but a coverage breakdown let Tony Gonzalez slip open in the endzone. Ryan found him, and everyone was stunned.
6. December 28, 2008. Week 17: Dolphins 24, Jets 17
Any number of games from 2008 can belong on this list, and either Dolphins game in 2009 could make this list. In fact by the time this game was played, the Jets' playoff chances were almost sealed shut. But this game was unbearable as a Jets fan. It was the culmination of a late season collapse that saw the Jets lose four of their last five games and miss the playoffs after an 8-3 start. This was especially bad because the Miami Dolphins completed a comeback from 1-15 to the playoffs, and the quarterback whom the Jets deemed not good enough to lead the Jets into the promised land was now winning the division for the rival Dolphins in the Jets' home stadium. Nobody knew exactly what went wrong, but the Jets rightfully cleaned house after the year, firing Eric Mangini, and cutting ties with Brett Favre. Mangini is probably going one-and-done in Cleveland, while Favre's Vikings have lost three straight after looking like world-beaters earlier. Maybe the Jets made the right decisions dumping them.
5. December 30, 2001. Week 16: Bills 14, Jets 9
One year after their horrendous collapse in 2000 (explained below), the Jets had a chance to clinch a playoff spot at home against an awful 2-12 Buffalo Bills squad playing their backup quarterback Alex Van Pelt. But it never is that easy with this team. Shawn Bryson and the Bills ran for 192 yards and the Jets fell behind early in a cold, blustery day at Giants Stadium. This would be higher on the list, but John Hall, the goat of 2000, drilled a 52-yard field goal to send the Jets into the playoffs the next week, so much was forgiven.
4. December 15, 2002. Week 15: Bears 20, Jets 13
The 2002 Jets' squad holds a special place in most Jets fans' hearts after the way they recovered from a 2-5 start to make the playoffs, but they almost choked it all away in week 15. The 3-10 Bears were led by Chris Chandler and they had touchdown runs by the other Adrian Peterson and former Jet Leon Johnson just to twist the knife in Jets fans hearts a little bit. Gang Green trailed 10-0 at halftime. Chad Morton returned the opening kickoff 97 yards for a touchdown, but wait, there was a penalty. The Jets trailed 20-13 and Pennington had one last chance. The Jets were moving the ball in for a chance at the game-tying score, when Wayne Chrebet opted to try to hurdle the entire Bears' defense. He fumbled the football, and the Bears won the game, sending the Jets to 7-7, where they would need everything to fall into place to make the playoffs. Sound familiar?
3. December 17, 2000. Week 16: Lions 10, Jets 7
In 2000 the Jets started 4-0 and then went to 6-1 before it all fell apart. The Monday Night Miracle and the famous Wayne Chrebet-Keyshawn Johnson game were wasted in Al Groh's first year. The Jets lost three straight to fall to 6-4, but then they bounced back with three straight wins to get to 9-4 and the precipice of the playoffs. All they needed was one more win. But the AFC West Champion Raiders destroyed the Jets in week 15 31-7, and with Ray Lewis and the future Super Bowl Champion 2000 Baltimore Ravens on deck, the home tilt with Detroit was the game the Jets needed to win the playoffs. The weather was just as bad as the team that day, but the Jets still led 7-3 most of the game. A late touchdown on a fumble recovery by Jeff Hartings, the Lions' left guard almost killed the Jets, but they had one last chance to send the game into overtime. John Hall then shanked a 35-yard field goal, leaving the Jets needing to beat the Ravens to get into the playoffs, bringing us to our number two game.
2. December 24, 2000. Week 17: Ravens 34, Jets 20
Despite back-to-back losses to the Raiders and Lions, the Jets had one last chance. Beat Ray Lewis, Chris McAllister, and the Ravens, and the playoffs were still there. Vinny Testaverde and company rolled up 524 yards, 382 more than Baltimore could manage, but it wasn't enough. Jermaine Lewis returned two punts for touchdowns, and McAllister intercepted Testaverde for a 98-yard touchdown near the end of the first half. The Jets had a game effort against one of the best defenses in the history of the NFL, but inexcusable mistakes once again cost the Jets a chance at the playoffs.
1. January 15, 2005. Divisional Round: Steelers 20, Jets 17
You knew this would be number one. The biggest heartbreak of the decade bar none. The Jets came off a game they did everything they could to try to lose the week before at San Diego to set up a showdown with the 15-1 Steelers. Ben Roethlisberger was a rookie sensation, but the Jets harassed him all game. Eventually, Doug Brien had a 47-yard attempt to take the lead with 2 minutes to go, which he just barely missed. However, David Barrett gave Brien a chance at redemption, intercepting Roethlisberger on the very next play, giving the Jets the ball at the Steeler 36. After getting one first down, Herman Edwards reigned in the offense, running the ball twice, and then having Pennington take a knee in the middle of the field rather than try to get a few more yards. As every Jets fan expected, Brien shanked the kick, and Pittsburgh won in overtime. The Jets reacted by drafting the best kicking prospect in years in the 2nd round the next year, and in typical Jets-fashion, he was a bust. The Jets haven't reached the divisional round since, much less the AFC Championship, which they were just a field goal away from.
Honorable mention: Too many to count.