I do a lot of listmaking; I have, for example this ranking of every Bay Area Championship team.
It will not surprise you that my assumption was that I'd be adding another this season, either at number 1 or number 2.
I thought about this list being the flip side of that, and I will still probably put together a "worst Bay Area Championship losses" list, but there's research there I presently don't have time to do.
This list will then focus on me and on pain - for me, which were the ten sharpest losses in my life.
10. September 30, 1997, October 1 1997, October 3, 2003, October 4, 2003
NL Division Series. Marlins
A four way tie would seemingly violate the principles underlying a Top Ten list; however, these are the four Miami games, four one run, last at bat playoff losses to the Marlins. I attended all of them; all 1 run late road losses. It was excruciating. Future Giants Edgar Renteria and Moises Alou walked us off with run scoring singles in '97, Jose Cruz dropped the ball in the 11th and then Pudge Rodriguez walked us off with a 2 run single in 2003, followed by JT Snow getting thrown out at the plate to end the game the next day. All 4 games as tight as they could be, all 4 road losses with me in attendance. I've never actually witnessed the Giants win a playoff game.
9. January 17, 1993 NFC Championship, January 23, 1994 NFC Championship. Cowboys
You gave me that tie at #10, I appreciate that, thanks, but I've pressed my luck with following it up with another. That's fair and I'd feel similarly. These are the back to back NFC Championship losses to the Cowboys in the early 90s and they're entirely blended in my mind. This was a white hot rivalry, probably the biggest in all of sports during the early 90s. These were the Steve Young teams, just tremendous regular season clubs, particularly that '92 club is as good as any of the great 49er teams but we just weren't as good as those Cowboy squads - Dallas, for reasons both historic (we also lost back to back title games in the early 70s) and cultural (who doesn't hate the Cowboys, the cheerleaders, America's team, they had a hole in the middle of the roof of the old stadium so god could watch - all that Landry/Staubach stuff) When the Cowboys are running high, as they were in the early 90s with Jimmy and Jerry, they are the most insufferable act in sports and these were tough, tough losses.
8. January 8, 1984 NFC Championship. Redskins
Two seasons after winning our first Super Bowl we were in DC, scoring 3 fourth quareter touchdowns in what looked to be an all time great NFL comeback win - but a couple of ungodly bad pass interference calls took it away from us. When you're 13, as I was for this game, nothing angers more than bad officiating.
7. October 13, 1987 Game 6 NLCS. Cardinals
The Giants had not played in a World Series in my lifetime, but led the Cards in the NLCS 3 Games to 2 - and then lost here 1-0 when Candy Maldonado misplayed a fly ball in the second inning. The Cards beat us in Game 7. I was barely 17 here, more a boy than not, and losses resonated deeply.
6. February 3, 2013 Super Bowl 47. Ravens
If I didn't have 5 Super Bowls in the bank, this game would be higher on the list, we were 22 down in the second half but climbed all the way back, failing to score four times from inside the 7 to lose the game. The Niners had been down for several years, emerging the season previous to lose the NFC Championship in overtime (if this were a 15 most painful losses, that would be there) so this season was part of what seemed to be a resurgence in 49er football.
5. January 19, 2014 NFC Championship. Seahawks
Accompanying the Niners early 2010s return to prominence came a hot feud with Seattle, unlike the Cowboys/Packers feuds of the 90s, this one ended quickly and ended here. The 49ers best player, NaVorro Bowman, had his leg half torn off just prior to what looked to be a game winning drive stopped by an interception in the end zone by Niners chief nemesis Richard Sherman. Why worse than the Super Bowl loss --both because it was a blood feud and because it felt like a tipping point, that after three straight soulcrushing ends of seasons there might be no way back up the mountain.
4. June 19, 2016 NBA Finals Game 7. Cavs
The impetus for the list; the Warriors, as much of a longtime doormat as Cleveland, surged to prominence in the 2010s, winning the NBA Title the year before and then breaking the longtime record for regular season wins with 73. We had a 3-1 series lead which seemed pretty clearly insurmountable (as no one has ever surmounted a 3-1 deficit) but lost games 5 and 6 and then a back and forth nailbiting game 7.
3. October 3, 1993. Last day of regular season. Dodgers.
The Giants, who were as close to leaving town as any team which stayed put ever got, signed Barry Bonds in the offseason and were 59-30 as of July 10, solidly the best team in baseball and staring at the first World Series championship since the move west.
And then the Braves got Fred McGriff - in a Wild Card free world, the Giants and Braves went toe to toe during the entire second half of the season, a real pennant race, one team advances, the other stays home. We won 103 games but lost to - of all teams - the Tommy Lasorda Dodgers on the last day of the season to finish second and miss the playoffs. It remains the second best regular season team in SFG history.
2. January 20, 1991 NFC Championship. Giants
Back to back Super Bowl wins and a clear path ahead to winning the NFC Championship turned into the virtual end of Joe Montana's 49er career in a matter of moments. This is the game most similar to Warriors/Cavs - the Niners were riding high and looking to make history and got caught short in shocking fashion.
1. October 26, 2002 Game 6 World Series. Angels
The Giants, who had never won a World Series since moving to San Francisco, were 8 outs away with a 4 run lead and lost. You know the thing in the movies where someone's trapped underneath a car and they're still conscious but there's no way to help and you just watch them die? That would rank 7th on this list.