Usopp is a sniper who grew up in Syrup Village, a town in East Blue. While in this village, Usopp became infamous for his many lies and fantastical tales. During this time, Usopp inspired the loyalty of some of the village children and they form their own 'pirate' crew, the Usopp Pirates.
After Luffy set out to become the Pirate King, he encountered Usopp and welcomed him to his crew. Since then, Usopp has been a great contributor towards the success of the Straw Hat's journey. Usopp dreams of one day becoming a brave warrior of the seas and, going by his trajectory so far, he will definitely get there someday.
10 Can't: BABY 5
Baby 5 is a former member of the Donquixote Family and a current member of the Happo Navy, after marrying Don Sai. Baby 5 consumed the Buki-Buki no Mi and became a weapon human.
With her ability, Baby 5 can turn into any weapon that her mind can conceive, making her a versatile and effective combatant. She was strong enough to make it into one of the most ruthless and notorious pirate crews in the New World.
9 Can: CHEW
Chew originally appeared in the Arlong arc, where he served as an officer in Arlong's pirate crew. In his time, he harmed many humans due to his belief that fish-men are inherently superior.
With that belief system, he, under Arlong's command, took control of Cocoyashi Village and ruled with an iron fist. Chew prefers to keep his distance during fights. As such, he usually shoots projectile timed attacks, which makes him a perfect opponent for Usopp.
8 Can't: WYPER
Wyper is a descendent of the Great Warrior Kalgara. He made his debut all the way back in the Skypeia arc and showed he was a warrior that could compete with Luffy and Zoro.
Wyper is a proud Shandorian warrior, who does not hesitate to throw his life on the line once it aids his goals. In Skypeia, Wyper showed incredible durability and fighting skills that impressed every Straw Hat that saw him do battle. With his physical ability and Reject Dials, Wyper would be sure to take down Usopp in a one on one duel.
7 Can: CHESS
Chess is a loyal subordinate of Wapol, the former King of the Drum Kingdom. During Wapol's exile from his homeland, Chess stood by his King's side as they took to the life of piracy. After Wapol returned to the Drum Kingdom in order to reclaim his throne, Chess accompanied him and, here, he did battle against Chopper and the Straw Hats.
Chess mainly fights using his bow and arrows, which he wields effectively. Despite his proficiencies as an archer, he is far from Usopp's level as a sniper.
6 Can't: HAJRUDIN
Hajrudin is the current captain of the New Giant Warrior Pirates, who happen to be a part of the Straw Hat Grand Fleet. That means a serious battle is unlikely to ever occur between the two characters. However, if they were to do battle now, then Hajrudin would most likely come out on top.
Hajrudin's giant body means he's incredibly durable, meaning it would be incredibly difficult for Usopp to deliver any significant amount of damage. Hajrudin's great strength means a couple of hits could be enough to permanently put Usopp out of commission.
5 Can: HAMMOND
As a member of Hody's rowdy little pirate group, Hammond was a fish-man who went up against the Straw Hats during the Fishman Island arc. Hammond didn't do much on Fishman Island. His biggest challenge was standing up to Luffy's Conqueror's Haki and even that proved too much for him to handle.
As a fish-man, Hammond is naturally several times stronger than a normal human and his animalistic senses greatly help him in combat. Despite these attributes, Usopp's growing strength means he could easily defeat Hammond.
4 Can't: VAN AUGUR
Just like Usopp, Van Augur originated from an island in the East Blue, before setting off on a journey that would lead him to become a member of a notorious pirate fleet. Augur is currently one of the strongest snipers in the One Piece world and is easily capable of sniping targets far beyond a human's natural field of vision.
Augur wields a long rifle known as Senriku, which shoots with deadly force. Usopp is a great sniper, but he is not yet at Van Augur's level, meaning, he would lose were the two to duel.
3 Can: MR. 5
"Gem of the Border" is a former member of the criminal organization, Baroque Works, where he operated under the alias of Mr. 5. Mr. 5 quit his life as an assassin to become a fireman, but before his retirement, he was a dangerous criminal.
After consuming the Bomb-Bomb fruit, Mr. 5 became a bomb-man, who could turn any part of his body into a bomb. This made him a natural weapon and he's even managed to overpower Usopp previously. Nevertheless, Usopp's continued growth and his time in the New World makes him a pirate that's now superior to the Gem of the Border.
2 Can't: YASOPP
Yasopp is the husband of Banchina and the biological father of Usopp. Just like his son, he is an impressive sniper who is greatly admired for his marksmanship. Yasopp is a powerful pirate that serves under the Emperor of the Sea, Red Hair Shanks. The Yonkou commanders are known for being frighteningly strong and, amongst them, Yasopp is considered one of the most powerful.
Yasopp's skill was so remarkable that his name spread to Shanks, who went in search of the great sniper. Since then, the two have ascended to the peak of piracy. Yasopp is probably the strongest sniper in the world, meaning he could defeat his son, Usopp, in a battle.
1 Can: VITO
Vito is the advisor of the Firetank Pirates, led by the Worst Generation member, Capone Gang Bege. Vito is a mixture of a deadly mafia hitman and an overly emotional and eager child. Vito often dreams up whimsical fantasy stories inspired by the adventure of his favorite heroes, the Germa 66.
Fortunately for Bege and his crew, Vito's personality doesn't hinder his abilities and, with his abnormally large hands, he can be a tricky combatant. Usopp has proven time and again that he's an incredibly resourceful fighter, which would greatly aid him in a battle against Vito. That versatility means that Usopp could adapt to Vito arsenal, which would bring him victory.