@Rogues':
The major problem here is literally anyone else could have replaced Ussop, anyone other character at all, and made that same gag expression from ingesting that same spicy sauce, and the result would have been identical to Sugar fainting. We thought that this was going to be a character-specific moment for Ussop and Ussop alone (like a particular technique or strategy that only he was capable of doing and thus rightfully earning the victory) and it flat out failed.
Ussop didn't earn this victory. He was conveniently bailed out of sudden death due to idiotic gag-based shenanigans he had no control or say over.
It's a Hollow victory. A win without meaning. There's no actual substance behind it, only vapid luck.
"But it's just like the fight with Perona Rogue, he won by scaring her too and that was also just a silly gag!!!"
No. No, it's not. The two aren't even remotely similar.
Those fake, plastic toy cockroaches that were crawling all over Perona? that was a deliberately planned attack by Ussop (the "Cockroach Star") same as his inflatable 10-Ton rubber Hammer (the "Ussop Golden Pound"). Again, both of those were clever techniques used to psychologically terrify Perona into unconsciousness. He was clearly outmatched by Perona's ghost abilities, but remained level-headed, thought the situation through, and had a clever strategy that matched his personality and capabilities to outwit her using various Halloween props. He had to prevail in that fight because, due to his overly pessimistic personality, he was the only Strawhat capable of facing Perona and staying immune to her negative ghosts. Should he have failed, Perona would have absolutely hunted down the rest of the crew and easily captured them. Zoro, Sanji, and Franky were all counting on him to succeed, and he did not let them down.
Here in Dressrosa? He spends the majority of his time in the underworld acting the coward (to the point of being frightened of useless Doflamingo underling fodder) and constantly planning to drop the dwarves like an ugly baby and leaving them to their fate while making a run for it if the plans goes south. When he actually does, he lays the blame for his cowardice squarely on Franky for giving him too difficult a task. When he finally mans up and returns to the dwarves aid, he gives him a much bravado-filled speech as to how he'll become - through hell or high water - the legendary hero they desperately need and prepares to face off against Trebol and Sugar. Cut to Ussop being absolutely mauled into unconsciousness without the slightest sign of physical damage or exhaustion on Trebol's part. Instead of simply turning their hero "Usoland" into a toy before the dwarves' eyes and further crushing their hopes into despair while simultaneously adding him to Doflamingo's workforce (a much more sadistic option) or instead of simply letting Trebol squash him, Sugar decides to plant the Tabasco-ball in Ussop's mouth and (she believes) poison him. What follows is Ussop's reaction to the spicy Tabasco and Sugar fainting. The key difference here is to remember that Ussop was beaten into literal unconsciousness. He had absolutely no control over his face-fault. It was not a strategy he had planned nor counted on. It was not even a clever ruse he improvised on the spot when he was backed into a corner by Trebol's strength. It was utterly and completely INCIDENTAL. A side-effect of Sugar's own meddling. Had Sugar not gave Ussop the Tabasco and merely thrown it away when she thought it was Poison, Ussop WOULD BE FUCKED. The Dwarves, Toys, Kyros, and Robin WOULD BE FUCKED. In Dressrosa, far more individuals were counting on Ussop to succeed than back on Thriller Bark, and he completely let them all down. He lost miserably and was saved by random happenstance chance.
"but Rogue, you didn't honestly expect him to beat Trebol did you lol? Trebol's like on the same power level as Pica and Diamante"
Did I expect Ussop to manhandle Trebol? No. Did I expect Ussop to cleverly use a new technique to KO Trebol? No.
What I did expect though is for Ussop to use his creativity and ingenuity to exploit Trebol's weaknesses. Remember a couple chapters back when Trebol told Leo that his sticky ooze is dangerously highly flammable? Yeah, I expected Ussop to capitalize on that. For all of Trebol's strength, perhaps being covered in FIRE and hit with a chain-reaction of explosions wouldn't have put him down for the count, but it would have preoccupied his limited attention span long enough for Ussop to legitimately defeat Sugar via a long-range distance slingshot attack. Thus Ussop actually deserving the victory and leaving Trebol for the newly-freed Coliseum gladiators to exact their sweet vengeance upon.
Not to disturb your rant or anything but what happened was off-paneled. Also about his face-fault, the dude used chalkboards and rubberbands as actual attacks pre-timeskip, it's really silly to even question whether a face-fault can surprise a kid. I said this before, as much as I don't like it, luck exists and can determine the winner, it's been true in One Piece as far as Alabasta (maybe Loguetown?). The lucky win here is actually more natural since it's Usopp's face (ugly baby right?) and Sugar was pretty sadistic, you also can't just take away his effort just cause he lost. About Usopp winning that way though, I also didn't like it but if you try to think what Oda was thinking, he could've done anything else, Usopp sniping it into her mouth, easy as pie but he chose this. Think about the example that would set, a 19 year old guy poisons a little girl and knocks her out, even if it's skillful sniping, maybe he just thought it wasn't worth it.