Yes he did. And the saddest thing is that there was nothing he could do about it. He was broken. The first case is shortly after ROTS when Vader was making his Sith lightsaber.
In Star Wars Canon, only Luke Skywalker can be acknowledged as the one who truly defeated Darth Vader.
Only one person could defeat Darth Vader once and for all. The spirit of Anakin Skywalker, long dormant, finally rose and overcame the dark side. While his body failed him, Anakin rose once again and defeated the Sith once and for all. Both Sidious and Vader met their ends that day, at the hands of Anakin Skywalker.
Vader defended the Emperor and he and Luke were locked in mortal combat. Luke lost control of his anger, viciously attacking Vader, finally beating him down and chopping off his hand with his lightsaber.
Darth Vader was the stronger of the two by far, but in most cases with lightsaber duels, the victor is the one with the strongest connection to the Force. Obi-Wan finished his last fight with Vader by hurling a barrage of rocks, and it's unlikely he had lost this level of power by A New Hope.
As Darth Vader, Skywalker was believed to have had roughly eight-tenths of the strength of the Emperor. Nevertheless, Vader wielded tremendous power and skill, enough to use the Force to overpower almost any opponent he could not defeat with his lightsaber.
Luke Skywalker
However, once Luke fully embraced his power in Star Wars: Return of the Jedi, he proved that he was indeed stronger than Darth Vader and struck his father down.
He slays Sidious and returns to Obi-Wan, begging for atonement by execution, only to be met with true forgiveness instead. But just as this fantasy Obi-Wan refuses to strike his former friend down, Vader refuses to turn his back on the dark.
Luke (post episode 6) not only was he able to achieve the raw power Anakin never could, but he had the advantage of learning from past Jedi (potentially including Anakin). Yoda, Palpatine is canonically more powerful than Vader, and Yoda is often regarded as (and shown) being equal to Palpatine.
It appeared that Darth Vader was more machine than we thought. His armor could be hacked and controlled by a device. In a turn of events, Darth Vader's right limb holding his dangerous scarlet lightsaber was moving of its own accord toward his neck. This was a dangerous weakness indeed.
Darth Vader : You have failed me for the last time, Admiral! Captain Piett? Captain Piett : Yes, my lord? Darth Vader : Make ready to land our troops beyond their energy field, and deploy the fleet, so that nothing gets off the system.
Some time later, he faced the Sith Lord Darth Vader. Infil'a put up a fierce fight against Vader, almost killing him by throwing the already damaged Sith Lord off of a cliff. Despite severe damage to his suit, Vader survived the fall, and repaired himself with parts from Infil'a's droid, Arex.
No, not at all. He had a softish spot for a handful of individuals and unlike many other Sith, Vader didn't generally kill innocent people for no reason - but he always hated the Jedi and he had no regrets about what happened to them.
Darth Vader Wins Battles While Thanos Wins Wars
However, Vader still served and answered to Emperor Palpatine at the end of the day.
He couldn't bring himself to kill Darth Vader, however, because he continues to associate him with the Anakin he trained as a boy. This is also the exact reason why Obi-Wan didn't kill Anakin on Mustafar despite the opportunity a decade earlier in Star Wars: Episode III - Revenge of the Sith.
There are certainly scenarios where Darth Vader would have the upper hand in a duel with Yoda, but in most cases, Yoda would be the more likely victor. Vader wields absurd levels of Force power during his dark side prime that would certainly rival Yoda's own abilities, but likely not exceed them.
One of the main reasons why Yoda would've won against Anakin is simply because he was far better trained than him. Yoda could see the moves his opponents were going to make before they made them; therefore, battling against Anakin would've put him at a far heavier advantage.
N'Kata Del Gormo was a Force-sensitive male Hysalrian Jedi Master who lived during the times of the Galactic Republic. According to legend, he found and trained Yoda and a Force-sensitive Human friend.
Anakin ultimately fulfilled his role as the Chosen One and brought balance to the Force, fulfilling Qui-Gon Jinn's belief in the prophecy that foretold Anakin's destiny. Accepting his fate, Anakin joined his Jedi mentors in death by becoming one with the Force.
DARK SIDE FRIDAY - Did you know Palpatine feared Qui-Gon Jinn? Palpatine was immensely powerful and he could see the future which made him very confident about pretty much anyone who stood against him.
Anakin admits to Obi-Wan that he has been arrogant and unappreciative of his training, and apologizes to his master. Obi-Wan assures Anakin that he is proud of him, telling him that he has become a "far greater Jedi than I could ever hope to be."
Introduced in the first film in the original Star Wars trilogy, Governor Tarkin is the Grand Moff of the Galactic Empire and commander of the Death Star.