Summary
The genius of the Uchiha clan, Sasuke is certainly one of the most incredible fighters to have ever existed in theNarutoseries. Sasuke has always been an incredible fighter, and over the years, he has had the opportunity to engage in some amazing battles.
From fighting members of his own clan to taking on characters capable of destroying the world, Sasuke has had to face it all with nothing but his own strength and wisdom to rely on. While Sasuke has had some incredibly triumphant moments, he has also lost some other battles terribly.

10Deidara
Winner: Sasuke Uchiha
Immediately after Sasuke left Orochimaru’s hideout, he was faced with some incredibly dangerous enemies and Deidara of the Akatsuki was one of them. This battle was quite an intense one and, given the Deidara was already on a level of the Kage at this point, Sasuke had to toil to win against him.
Without incredible mastery of the Sharingan, Sasuke would certainly have lost. However, by this point, he was an incredible user of this eye. He was able to use his incredible intelligence, and coupled it well with the power of the Dojutsu he was blessed with. Sasuke was able to trick Deidara and completely outclass him in battle.

9Danzo Shimura
Danzo is a character that Sasuke fought after the events of the Five Kage Summit. Sasuke wanted to exact revenge on the Village Elders for making Itachi kill the entire clan. As such, he confronted Danzo and battled him in a ferocious manner. Despite having access to Hashirama’s cells and, on top of that, Izanagi, he was not able to best Sasuke.
Sasuke’s keen intellect was able to see through everything that Danzo threw his way, and he stabbed him right through the heart with a powerful Chidori, before he ended himself with a Reverse Tetragram Seal.

8Lightning Ay
Winner: Draw
In the Five Kage Summit, Sasuke actually ended up fighting against some very powerful enemies, such as the Fourth Raikage, Ay. Ay was quite a powerful enemy for Sasuke to take on. With his lightning armor, Sasuke was not able to pierce or injure him significantly.
This is a battle that Sasuke was getting completely overwhelmed in and could have lost had it not been interrupted. This fight did not have any clear winner.

7Kabuto Yakushi
Winner: Sasuke Uchiha (Through Itachi)
Kabuto Yakushi was an ally of Sasuke at one point, however, later down the line, these two ended up fighting against each other.
Sasuke had the aid of Itachi in this fight, and, together, the goal here was to get Kabuto to release the Edo Tensei. Itachi did the bulk of the work in this fight and together, these two brothers ended up triumphant.

6Killer Bee
Winner: Draw (With Help From Taka)
The Jinchuriki of the Eight Tails, Killer Bee is a character who ended up fighting Sasuke when the Uchiha went to retrieve him for the Akatsuki. This was quite an amazing fight as Sasuke could have died multiple times here. Killer Bee kept defeating Sasuke repeatedly, however, in the end, Sasuke received quite a lot of aid from his allies.
Sasuke also managed to learn more about his eye and its abilities and, because of that, injured Bee greatly. However, he was ultimately fooled into thinking that he defeated him, when Bee had actually managed to escape.

5Itachi Uchiha
Sasuke’s fight against his brother,Itachi Uchiha, is one of the best fightsin the entireNarutoseries. In this fight, Sasuke tested his skill against his brother, without even knowing that Itachi couldn’t even see at this point in the story and that he was actually waiting to die at his brother’s hands.
Regardless, this was an amazing fight in which Sasuke threw everything at him, and, in the end, managed to win. Itachi ended up falling in this fight and it was only after Sasuke’s victory that he found out the truth about his brother.

4Obito Uchiha
Winner: Sasuke (With Naruto And Shinobi Alliance)
Obito Uchiha is yet another incredibly powerful individualthat Sasuke ended up fighting. At one point, these two were working together, however, in the Fourth Great Ninja War, Sasuke ended up fighting against him and he became the 10 Tails Jinchuriki.
Along with Naruto, Sasuke was able to play a part in beating him and, in the end, thanks to the Shinobi Alliance, all the Tailed Beasts were pulled out of his body.

3Naruto Uzumaki
Winner: Naruto Uzumaki
Sasuke fought against Naruto multiple times in the series.While their first battle resulted in Sasuke winning, the second one turned out differently.
Sasuke, despite having the Tailed Beasts at his disposal, was not able to defeat Naruto. In the end, Sasuke and Naruto knocked each other out and Sasuke openly admitted to losing to him, changing his ways from there onwards.

2Madara Uchiha
Winner: None
Undoubtedly,the ghost of the Uchiha clan, Madarais one of the strongest characters that Sasuke has ever fought. When Madara returned in the 4th Great Ninja War, Sasuke took him on in combat.
Sasuke was easily overwhelmed by him at first, but after he awakened his Rinnegan, he was actually able to take the upper hand over him. Unfortunately, this fight was interrupted as Madara’s body was turned into a vessel for Kaguya’s return by Zetsu.

1Kaguya Otsutsuki
Winner: Sasuke (With Team 7)
Sasuke’s strongest enemy in the Naruto series was Kaguya Otsutsuki, by far. Kaguya returned when Madara’s body was used as a vessel by Zetsu, and, from then onwards, this fight was up to Naruto and Sasuke to win.
These two worked incredibly well together and overwhelmed her and, later on, the other members of Team 7 pitched in and helped them seal her away. The winners in this fight were none other than the members of Team 7.