Name a situation when you felt sorry for a fighter the most?

Yall arent gonna like this, and im a HUGE silva fan, but...

I really felt bad for cheal not getting the belt from silva, he was so close...

"what would you tell your father if he was here right now?"
"...I'd just tell him i tried..."
 
He lost 4 in a row after the Robbie fight, getting finished in 3 of them. In his last fight, he beat a guy who's lost 5 out of 6 fights, and 7 out of his last 10. Court has 3 wins in the last 5 years, and all 3 of the guys he beat were subsequently cut by the UFC. Not that Fight Matrix is the holy grail, but they have Court as the #97 WW. The guy should have been cut from the UFC years ago; he hasn't been UFC-caliber for a very long time.

So no, getting a decision over Court McGee doesn't equate to "looking good."

I see and appreciate your point but I wasn't equating looked good with winning a decision over Court McGee. I think looking good is something we can appreciate in a performance to some extent even when the competition is subpar. When a top fighter gets an unranked opponent as a late replacement, say, we can still see superior skill on display and realise that even if many fighters lower down the food chain could have beaten that opponent, they couldn't have done so in the same style.

For that matter, I can likewise make an independent assessment of Court McGee and determine that, even if his record his weak, he didn't fight badly against Condit. Your criteria imply that when two guys on skids meet, their fight is necessarily going to be substandard Maybe in many cases it will be, but in my eyes, Condit and McGee defied the odds and put on a good show.
 
For me its the smashing machine, mark kerr. Watching that when it first came out broke my heart. Seeing some Gary Goodridge interviews are brutal, especially when he talks about his CTE. Recently when Tony Ferguson lost, that made me sad, but happy for Justin.
 
Holloway losing is always heart breaking because they always film his kid crying.
 
Even though I was pulling for Edgar, I felt sorry for Maynard when he got stopped in the third fight. He was 1-0-1 going into the trilogy, and if memory serves he once again had Edgar dead to rights. Then Edgar rallies like a movie character and stops him. I can't imagine what he must've felt like coming to and realizing what happened.
 
Stipe Miocic when he lost the HW belt to Cormier. Granted, this was the day Cormier became double champ and it was a glorious moment but Stipe was too much of a nice guy to make excuses that eye pokes affected how that fight would have gone down drastically.
 
08_johnson_vs_brenneman_002.jpg

When Rumble kicked Charlie "The Spaniard" Brennerman at into space at WW. But Charlie was a tough dude who always went out on his shield.
 
It's worse when you're in the stands and witness it in person...

1. DC after Jones finished him. Bad enough to lose to your hated nemesis yet again. But the way he was corralled and cajoled into a postfight interview was wrenching to see. You could tell he just wanted to go away and recover his composure in private. But nope, they made him go on the mic to deliver a blubbery speech that still gets mocked by some people to this day.
(That being said, <DCrying>is too damn good a gif to refrain from using.)

2. Stipe after DC finished him. One moment he's "the baddest man on the planet", and the next he's being referred to as a piece of shit by a pro wrestler while he's still standing there in the Octagon. Waiting patiently, patiently for a postfight interview to have his say, but DC and Brock are so caught up in their stupid little promo skit that he's never given the chance.
 
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