Obi-Wan Kenobi - Maul and Grievous have both fought Kenobi bitterly on several occasions, but I'm leaning Maul. It's just much more personal between the two of them.
Darth Vader - Obi-Wan Kenobi, no question.
Anakin Skywalker - Count Dooku. Asajj is just too small-potatoes for Anakin in Canon. But Dooku was the one that consistently bested Anakin for years, with Anakin steadily getting closer and closer to victory. Also, Dooku took his arm, so it was only natural that he wanted revenge.
Darth Sidious - Luke Skywalker. Yoda may have truly been Palpatine's match, but quite frankly Sidious was running laps around the whole Jedi Order with his schemes. Yoda was never once one step ahead of Palpatine, and usually wasn't even in the same ballpark. Anakin may have been destined to destroy Sidious, but Palpatine was quick to twist that prophecy toward his own ends and use the "chosen one" as his own personal butcher. Rey wasn't much of a rival or threat to Palpatine until right at the very end when she channeled all of the Jedi. Luke is the only one who consistently threw a wrench in Palpatine's schemes, disrupted his plans for galactic conquest, and even turned his greatest asset against him.
Luke Skywalker - Darth Vader, without a doubt. Luke spent 3 years thirsting for revenge against Vader for having killed Ben. Vader was his big bad. Sidious was a much more nebulous threat rather than a personal one, and the rivalry between Snoke and Luke seemed pretty one-sided (Snoke was paranoid as heck about Luke, sounds like Luke slapped him down pretty hard).
Ahsoka Tano - Darth Vader is the only one who Ahsoka actually had personal stakes with. She may have dueled Asajj and Maul each on more than one occasion, but with Asajj it was more just incidental on account of the war. With Maul, she was typically just a road-block in his schemes.
Kanan Jarrus - Grand Inquisitor. Much like Dooku to Anakin, the Grand Inquisitor was a measuring stick by which we saw Kanan's steady growth. He started out consistently defeating Kanan at every turn, until Kanan was finally strong enough to stand up to him directly.
Composite Quinlan Vos - Don't know enough about Quinlan's Legends history (still working my way through collecting all the old Dark Horse comics), so I'll abstain from this one.
Darth Maul - Kenobi. Kenobi took everything from Maul when he cut him in half. Maul believed he was supposed to be what Vader became, the right hand of the Galactic Emperor himself. Kenobi robbed him of his destiny, and so Maul dedicated his life to Kenobi's downfall.
Assaj Ventress - I'm gonna go with an option not listed: Count Dooku. He turned her into his killing machine, then tossed her aside seemingly on a whim (she didn't know about Palpatine's order to have her killed). She then dedicated herself to Dooku's fall, working alongside the Nightsisters in ploy after ploy to destroy the Sith Apprentice until he commanded the complete and utter destruction of her people. Even then, when Vos showed up, she jumped right back on that bandwagon and attempted to bring down Dooku, only to meet a grisly fate at his hands.
For Obi Wan Kenobi - Darth Vader
For Darth Vader - Obi Wan Kenobi
For Anakin Skywalker - Count Dooku
For Darth Sidious - Luke Skywalker
For Luke Skywalker - Darth Vader
For Ahsoka Tano - Darth Vader
For Kanan Jarrus - Darth Maul
For Composite Quinlan Vos - Count Dooku
For Darth Maul - Obi Wan Kenobi
For Asajj Ventress - Obi Wan Kenobi (Count Dooku in CANON)
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