This is in no particular order before people start coming for my head. Yes, these are fights that hurt everyone differently. Though this is the order for me on what hurt the most and will keep waking me up in the middle of the night.
Gaara Vs. Rock Lee

Bro this damn fight gets me every single time. Having me stressed during and balling my eyes out for hours afterwards.
Rock Lee opens the fifth gate and everything turns into a nightmare.
Gaara using his sand coffin Jutsu Lee’s arm and leg.
Lee trained so hard to be able to keep up with opponents that are stronger than him. He could only use taijutsu. That was all just ripped away from him because of Gaara and himself.
Gaara threw me for a loop because multiple times I thought he was done for. Though this fight and him watching the one before really brought his inner demon out. He is absolutely ruthless. This was the fight that made me hate him.
Gaara was pretty much untouchable before this point, but Lee was able to get through the barriers.
Hinata Vs. Neji

Bro this was so painful to watch.
Hinata really holds her own in this fight, but Neji immediately is trying to cut off her chakra points and going for the kill.
It is absolutely adorable how she is moved by Naruto. She doesn’t want to be seen as weak or less than. She would rather be beaten and bruised like Naruto. He gives her strength.
The whole time I’m over here hoping girly would just stay the hell down. God, I didn’t want her to get hurt anymore.
They both don’t hold back, but Neji is just a little more stronger. He hits her main Chakra point and she goes into cardiac arrest.
Naruto Vs. Gaara

This is the fight that absolutely broke my heart for Gaara. We get his backstory and by that you understand why he is the way he is.
These two grew up very similar, but turned out differently. Both were rejected by the people in their villages because of the tailed beasts that are in them. They were alone.
The difference though, people came alone that didn’t fear and actually cared about Naruto. He remembers the darkness he felt and wonders if he would have ended up as bad as Gaara did. Gaara is so lonely, even his siblings are terrified of him. So he doesn’t understand caring for other people and wanting to protect them.
Both are so determined to win. Though they have different ways and they are shown in this fight clearly. When you have people you care about and want to fight for instead of just doing it for yourself tends to be just a little bit stronger.
Gaara Vs. Sasuke (Out of the Arena)

Sasuke and Gaara are the same when it comes to their feelings.
They are lonely. Which makes them want to prove they are better or more powerful. I believe it makes them feel more alive than what they feel on a normal basis.
Gaara enjoyed fighting Sasuke because he got to feel what pain looked like, but he was also able to give him a run for his money.
Unlike the first fight, Sasuke ends up not being able to push on.
This is when we start getting more of Gaara’s back story.
Gaara Vs. Sasuke (In the Arena)

The rent was due and they were absolutely serving.
Still hating Gaara at this point.
Hoping Sasuke beats his ass.
Might I say he does a pretty good job at it. Becoming the first person to make Gaara bleed is impressive. With Lee’s taijutsu and Kakashi’s chidori. He had succeeded Genin level.
Besides that, what the hell was that hand? The one that came out of the sand shell afterwards.
Absolutely threw me for a loop. Even being told what Gaara actually is, it was still pretty shocking. We only see part of his tail beast and not for very long.
But… Being the first time watching that scene I was over here thinking Sasuke was done for.
Sasuke almost drained all of Gaara’s chakra. The match didn’t really end, it was just switched to an actual mission.
Sasuke Vs. Zaku

Zaku didn’t stand a chance against the new version of Sasuke. So much that Dosu decided to hand over their scroll and leave.
The curse is awakened and the strength he has is unmatched. He had a new profound darkness hanging over everyone. A stronger presence that was scary.
So much that Sakura stepped in to snap Sasuke out of what was brought over him.
There is always that one fight where everyone knows that character is going to change forever.
Team 7 Vs. Orochimaru

This fight was insane.
Naruto and Sasuke really lock in at some moments, but it’s not enough going against Orochimaru.
Realizing that this changes everything. Sasuke is now cursed, Naruto has the nine tails locked in him even more, and Sakura is trying to figure out how to help, but not really.
Having my anxiety going to the point of overload wondering if anything after this is going to be the Naruto I first started watching.
Naruto Vs. Neji

Naruto finally channelling the Nine Tails
Neji and the 64 palms.
My heart slowly started opening up to Neji. He was objected to a curse mark. The mindset he has makes sense. Being born to practically be a slave to the main branch family.
It was like he thought he really couldn’t succeed at anything higher than that position.
Naruto proves to Neji that destiny can be changed if you try hard enough.
Naruto believes that if you work hard enough you could do anything you put your mind to. He seems to even exceed what people think about him time and time again.
Honorably Mentioned:
Anko Vs. Orochimaru

Anko using a forbidden Jutsu that Orochimaru taught her. Now what was she thinking?
Which my question was so accurate cause she should have known that he was going to get out of it. Like what a death sentence for 2 turned into 1.
GIRL HE IS THE ONE THAT TAUGHT YOU!!!!
Gaara Vs. Team Shigure

Seeing Gaara’s skill level is absolutely terrifying.
Not flinching to kill Team Shigure. Then threatening his own siblings. Here you will think Gaara is heartless and there isn’t a way to get through to him.
Gaara didn’t even have to put in any effort into fighting them, it was strictly child’s play to him.
Naruto Vs. Kiba

Farting in Kiba’s face was insane. I mean whatever works.
For a good minute I really didn’t think Naruto would win. Let’s be honest though, he doesn’t give up.
This is probably the fight where everyone stopped doubting Naruto. Just a little, he had grown more than people had realized.
Temari Vs. Tenten

A Wind Jutsu against a weaponry specialist.
Tenten was completely outmatched against Temari. It was embarrassing to watch.
I’m not saying she is bad with the skill set she has. It is just a weapon that can’t reach their target are useless against certain opponents.
Also can’t we just talk about the fact that Tenten’s back gotta be broken after landing on Temari’s fan like that. Then trying to throw her into her own weapons was absolutely diabolical.
Orochimaru Vs. The 3rd Hokage

This fight was stressful, but I didn’t really care about the third Hokage in the first place. I will say he does make me cry with his speech about protecting the village. Other than that the power level we get in this fight is very much out of this world. You can really tell how these people are so powerful.
The 1st Hokage can create a full forest.
The 2nd Hokage is able to create a TSUNAMAI!
The 3rd Hokage making a fireball as big as a dragon?
Orochimaru can replace other people’s souls with his soul.
What in the world has this turned into.
The 3rd Hokage dies while trying to seal Orochimaru, but just kills his arms and nothing else sadly.
What fight wrecked your emotions bad enough that you wake up at 3am to ponder on?
Need a palate cleanser after all that emotional damage? Too bad. Naruto’s over here.
