OT: Most Painful/Heartbreaking Sports Memories?

These are all fantastic and many are on my list too. But I also add losing to Duluth in overtime in 2011, my heart fucking sank. Also not a big baseball or softball guy, but the baseball loss to vandy was tough since it was such a run, and softball losing to Florida in title games. These felt like all Michigan athletics would always be the bridesmaid never the bride. 

JT was short

Trouble with the snap

Appalachian State

10-10 tie, vote OSU to Rose Bowl

Tripping Desmond in the end zone

90 Rose Bowl, ref screw job

Phantom TD Charles White

TCU playoff game

27-20 Washington Rose Bowl game

1. Loss to TCU

2. Trey's block. The Louisville fans I dealt with on a daily basis were insufferable. 

3. That horrible ball spot in the OSU game

4. That MSU blocked punt

I think most of them are covered. The only ones I see missing are the 2009 Stanley Cup Finals and 1996 Western Conference Finals. In 2009, the Wings were up 2 games to 0 then 3 games to 2 before losing games six and seven both by 2-1 scores. 1996 was just a total let down and made most Wings believe that they would never get over the hump which they eventually did.

No UM stuff, to many to forget.

Dick McAuliffe hitting into a season ending double play in 67. Needing to win the 2nd game of the doubleheader McAuliffe hits into his only double play of the season. Boston goes on to win the pennant.

Kordell Stewart.

MSU Punt Block.

Desmond was Tripped.

The Block was Clean.

For me it's a very close call between Webber's timeout and the 2016 OSU game.  

I was in middle school when the Fab Five played - prime formative sports fandom.  Michigan had won it all in '89 but that already seemed like forever ago by the time the Fabs arrived.  They vowed to return to the title game after the '92 loss and did it!  It seemed like destiny.  They had their shot, down 2 with 20 seconds left and the ball, for the national title ... and then C-Webb called timeout.  Brutal.  

That's still painful to think about, especially considering that we have never won another national title in basketball (and even more when we're terrible again).

2016 was the chance to let go of a decade of pain and was right there in our grasp, until the refs ruled otherwise.  This felt even worse as the next four years progressed and it looked like that might have been the high-water mark for the Harbaugh era.  Thank goodness it wasn't!

Jim Kemerling cheating Bo’s last Rose Bowl game with a BS hold call on the fake punt.

Charles White phantom TD Rose Bowl.

MSU time keeper Bob.

Lloyd rushes three and wastes a LB 10 yards to give Kordell Stewart time throw a 60 yard bomb.

Block was clean.

JT was short. We win that game, we are looking at a playoff run and possibly a national championship. Sure, we got that championship a few years later, but that was back when Jim was killing it on the recruiting trail - that win could have set us up for a Bama like 5-7 year run. 

2018 The Game. Lost to Uncle Urban after it was revealed he covered up domestic violence allegations made that loss STING. 

2009 SCF Game 7: losing to that crybaby Crosby when we were the better team and then Crosby getting away with snubbing Wings in handshake line made that loss STING. 

2016 The Game: JT was short. But people aren’t pointing out what led up to that. ZERO live action penalties called on Ohio in that game. Refs did not give UM a fair shake. 

Good list, you hit most of the ones I thought of.  I’d add

1987 Tigers - won the AL East after one of the great pennant chases with the Blue Jays.  We one the one game playoff and then proceeded to lose to an inferior Twins team in the ALCS.  George Bell edged Tram for MVP also.

88 and 89 Pistons - Bird steals the ball, phantom fouls and the Dantley / VJ collision.

1994 - Kordell Stewart.

1988 NBA finals (though 89 and 90 blunt that pain a bit) and 2006 World Series.  For Michigan, definitely the 2013 NCAA championship game

Wimbledon 2019 

Federer looses to Djokovic in 5 sets after having 2 championship points on his serve. Devastating knowing that was his last chance at a major and the narrative ramifications. Djokovic and Nadal probably still would have broken his record, but who knows how different things go if he wins that one. 

1. The game winning hit off Mariano in the 2001 World Series.

2. The Knicks losing the championship to the Rockets. 

3. The fumbled punt against MSU.

4. JT was short.

5. The block was clean. 

6. The Yankees losing the World Series to the Dodgers in 1980 (?).

7. The RichRod/Hoke years.

Bird's Steal was my first sports gut punch.  Others:

JT was Short

1955 Chokers (1996 Wings-Avs Conference Final)

1994 Hail Mary

Big Papi grand slam

I literally cried when Eddie Oh outscored UM 12-10 and gave ND a win they didn't deserve. (IMHO....) I hated how Musburger GUSHED over the kid, like it was some great college football story or something. (It was....) Didn't he know my beloved Wolverines were victims of this, this, heinous outcome? I' mean, they didn't even score a touchdown? How could that happen?!?!?!?

Of course, I was not yet 5 years old, but I still remember that one.

This might sound crazypants or seriously insane rationalization, but...

Let's say we punt cleanly vs MSU in 2015, and they still upset OSU in the toilet seat later that year.

In that scenario, there's a VERY probable world where they win the B1G and make the playoffs (those two things are almost assured), and repeat.  They might still have lost against either Bama or Clemson, but I dunno that I'd want to roll the dice on that, especially since it was largely the same team that won it all the previous year.

Yes, losing to Sparty sucks, but if it was a binary choice between that game vs OSU getting another national title, I'd fall on that sword seven days a week and twice on Saturday.

1972 AFC Championship game (Dolphins over Steelers). Game was played in Pittsburgh despite Miami being undefeated, as in those days the host site rotated. Miami did outgain the Steelers but they were very fortunate to win. After attending the Immaculate Reception game the prior week, that was quite a comedown, also in person.

1993 Patrick Division finals, NY Islanders over Pittsburgh in OT of game seven. The Pens were two-time defending champs and had tied game seven with two late goals. In retrospect, they likely were too injury-riddled to have beaten the Patrick Roy-led Canadiens in the next round anyway, but it didn't feel that way at the time.

J.T. was short. I now wonder if Jim would've left sooner if he'd beaten Ohio prior to 2021, but the officiating in that game was way beyond home-town reffing, and not just on that fourth-down play.

In the 1980’s it seemed like we would never beat the UNC Tarheels in basketball.  I lived through these NCAA tournaments:

‘85 - 1 seed MI lost to 8 seed Villanova in round 2.  ‘Nova went on to a Cinderella National Championship.  A buddy broke my TV when he knocked it off the stand in the closing moments.

‘86 - 2 seed MI loss to 7 seed Iowa State in round 2.

‘87 - 9 seed MI lost to 1 seed UNC in round 2.

‘88 - 3 seed MI lost to 2 seed UNC in round 3.

SPOILER ALERT!

‘89 - 3 seed MI beat 2 seed UNC in round 3, followed by a 102-65 thrashing of 5 seed Virginia to advance to the Final Four.  The Virginia game was the most fun I ever had watching a game on TV.

I was in Seattle for wins over Illinois and Seton Hall for the National Championship.

2009, Tigers lose the tie breaker for the central division in extra innings.  We had been all in since 2006, even kept our tickets for a year after moving to Texas.  It didn’t help that my friend who had started me down the road to baseball fandom was losing his battle with cancer.  He made it another month.

Watched on TV on a Monday night.  The only time I ever full-on bawled about a sporting event.  

1994 Colorado.  

Colorado fans are some of the worst kind of entitled, “born on 3rd base” types.  When the Nordiques moved here and won Stanley Cups (in no small part because of their felonious goal tender), they thought just buying tickets and attending a few games conferred lifelong fandom.  

CU’s unexpected, sudden success in the 1990s was similar.  So living here and having to hear “Hail Mary” from the kid bagging my groceries was tough to take.  Not bad enough to get me to move away though.  And we ultimately got ours, which is what being a fan is all about.  

1995 NCAA hockey tournament - triple overtime loss to Maine in the semis

2018 NCAA hockey tournament - gave up a goal to Notre Dame with just over 5 seconds left in the game to lose 4-3 (after having been up 2-0)

Colorado bomb…

Most painful: Basketball 1993 vs. UNC

Most bitter: Football 2016 vs. OSU

Most memorable (non-obvious category): Football 2003 vs. Oregon. As I recall they led 21-6 at halftime and melted down in the second half in a perfect storm of special teams errors, poor coaching, and shaky officiating.

Worst non-Michigan memory: Being at the last game at Veterans Stadium when Ronde Barber and the Buccaneers recorded the first franchise victory in a game under 40 degrees (?) to beat the Eagles in the NFC Championship.
 

Cordell's last second TD for a Colorado victory at the big house. The refs not marking the correct spot when UM stopped OSU on 4th down in 2016. Losing to the Gophers in 1986 when we were the number 2 team in the country.

I was there in person for several of those games (most recently the Lions in Santa Clara). 
 

I would add 2009 Red Wings Stanley Game 7. 2015 Michigan State football. 2018 Ohio State football game. 1994 Colorado football game. 1988-89 Notre Dame football. The fuckin ‘13 NCAA MBB title game. 

Basically any osu loss but in order.. 

2016 hurt the most.  Out played them by a massive amount. The officiating in that game from start to finish was flat BS!  I will never count that game as a loss!  I don't count it as a win given it will never count as a win just never see it as a loss just a complete screw job. 

2017/2018 vs osu same bs with officials. 

The toughest losses outside of these come back to a few. 

2006 Osu, that late hit hurt.. that game hurt.  The fact that officials called the late hit and never called the lber for jacking Manningham was straight bs. 

Most painful outside of osu. 

TCU after winning the natty the pain of this loss and most all of these losses really subsided.  But it stings because I thought we had a serious shot with Georgia and a shot at redemption.  Idk if we win that game but I wanted to see it. 

2016 OB loss to fsu also stung, to get back into that game and blow it the way we did stung.  It just felt like all the wind was out of the sails of the program for a bit after that. 

a lot of coverage of Michigan Football and Basketball moments.  I attended Michigan 98-03 and Michigan had some great hockey teams that lost in the frozen 4 to amazing goal tending games.  Would have been cool to see Michigan win the National Championship in Hockey. My Brother said that after the 98 win, the celebrating mob ended up outside of Bollinger's presidential house on campus who invited them in to celebrate. 

1977 ALCS Freddie Patek in dugout after loss to damn Yankees

2015 msu for sure. Harbaugh’s first season, we were on a 4 game win streak and msu was undefeated but vulnerable. Little bro was put back in their place and it was over until it wasn’t. I was stunned in disbelief and it took me two weeks to process what had happened.

Big Nut's