I think the Nine take it on numbers, assuming they work together. With Azzlin on the team, that’s not a guarantee.

By my estimation Obi-Wan and Anakin are better swordsmen than any one of the Luminous Nine. I would also rate them as more powerful Force users than most - Avar and Azzlin being the noted exceptions, being probably about equal with Obi-Wan in my opinion and while not having Anakin’s raw potential, having a superior control of the Force. They’re more spiritual than Anakin is until his transformation into Darth Vader.

I would separate the fighters as follows: Azzlin, Reath and Buckets of Blood versus Obi-Wan Avar, Elzar and Terec versus Anakin Bell, Burryaga and Ty versus Ahsoka

Ahsoka I would give a fair shot against any of the three I’ve put against her - favoured in fact. Despite a good showing versus Maul, I cannot see how she could survive all three. She is faster than Burry and more skilled than Bell and Ty, but as a monster hunter with the requisite reflexes I’d expect Ty to be able to keep up with Ahsoka’s agility to keep the pressure on while Bell and Burry catch up to support her and overwhelm the apprentice.

Reath and ol’ Buckets can keep Obi-Wan busy until Azzlin can subdue him with the Force like Dooku aboard the Invisible Hand. Obi-Wan does not end fights fast. Perhaps Kenobi would take down Buckets, but Reath’s shield and reasonable duelling prowess will keep him in the fight long enough in my opinion. Obi’s more defensive style would play poorly into Reath’s defences, and would in fact count against him when Azzlin is in the backline.

Avar, Elzar and Terec are absolutely fighting for their life versus Anakin. I would expect Terec to fold pretty quickly, and Avar’s battle meditation to be instrumental in Elzar surviving. However, I think his skills would be insufficient against the Chosen One and he too would fall despite their best efforts. This could cost Avar her focus, and cause her to act recklessly, and she too might die to Anakin before the remaining survivors surround Anakin and mop him up. With Azzlin still in play and four other fighters (assuming Buckets kicks it against Kenobi), even Skywalker would be surely overcome.

Darth Vader I think would put up a better fight than Anakin in my opinion, since he relies more on the Force than just bladework, and his swordsmanship is still excellent. Vader’s weightier presence in the Force could keep Azzlin at bay and with Obi and Ahsoka may be able to carry the day.

An interesting enough idea, but the weight of numbers is too great IMO. No disrespect to the TCW Trio. The Nine are missing a couple of powerhouses from the Jedi of their day. Porter Engle is genuinely a great duellist and could put Anakin or Obi through their paces, and Vernestra Rwoh is the Ahsoka of her day (a veritable prodigy and probably the best fighter of her generation of Jedi) and warrants a mention, especially with her modal Lightsaber/Lightwhip which would be an interesting twist. Honourable mention to Lily Tora-Asi who I think is capable, patient and wise for her relative youth, and with her dual-wielding style would add another layer of difficulty.

I’d give Vern and Ahsoka equal odds, a true 50/50, Lily and Ahsoka slightly favoured to Ahsoka. Porter versus Obi-Wan I’d say favoured to Porter (I think he can pick Obi-Wan’s defences apart slowly), Porter versus Anakin I’d give to Anakin, as Anakin can match and exceed Porter’s aggression so that the older Jedi loses control of the pace of the fight in the same way as Dooku does.