I can see the Chaotix beating Team Dark, and before you come at me.
One: In good stories fights aren't won with power-scaling. They're won with planning, strategy, and techniques.
Two: This is not to say Chaotix are "stronger" than Team Dark, it's more to say that in a seemingly one sided battle. They could win without it feeling out of place.
If your willing to be open minded please continue.
One thing I've noticed about Team Dark lately is that they work around each other, but not with each other. Shadow will disobey or outright ignore orders from Rouge. While Omega just does his own thing. Granted they work well together because they know how to work around each other, and they still care about each other. However as a team. They really don't feel like one anymore. More like a friend group if that makes sense.
A major part of it, is how Shadow's character has changed. Yes, he's always been confident and boastful. Compare how he acts towards his team in Heroes and 06 to how it is now. He went from confident to outright egotistical. And while there is a shift in easing that back, I think his character being humbled would be good for him.
That's where the Chaotix come in. Now they're very messy all things considered, but they do work well together. For the most part Espio and Charmy will listens to Vectors orders. Now successfully completing those orders or needing to be reeled back is another thing. Even then, the rare times we see any form of resilience is from very strong feelings. Like Charmy wanting to rescue a citizen during Zombots, or Espio questioning Vectors evacuation plan. The former has been the only time Charmy has outright disobeyed Vector, but it wasn't a lack of respect for Vector, but a willingness to try and help someone no matter what. While Espio was fine with Vectors plan after he had explained his reasoning. It reminds me of how Team Dark used to be.
So honestly I'm not sure how the battle would go, but I can say. Vector is tactical and observant. Yes, he may act like a clown, but he is much smarter than people give him credit for. I would even argue that Vectors deductive skills are on par with Tails mechanical and scientific skills. Another thing is that Espio is a truly talented ninja. Sure it's played for laughs sometimes, but he is still capable.
It would be a battle where the Chaotix win, because they're able to work together and formulate a plan to trick Team Dark into losing. It can even be a case of winning the war, but not the battle. Where they use the fight as a distraction for their actual goal. (Like during the chaos Espio switches the real McGuffin for a fake one that Team Dark "wins")
I think it would be more meaningful if the reason Team Dark lost was because of Shadow. The most powerful off the team. Because his ego was so large, and he refused to listen to Rouge at all. I can see Rouge being able to spot that Vector is planning something in regards to what Shadow is doing. While she isn't exactly sure at the moment, she does know her team needs to be cautious until she figures it out. Instead of Shadow listening to her, and being much more defensive. He instead basically tries to solo carry, and he is the reason they lose.
Shadow the Hedgehog the Ultimate Lifeform. Not defeated by his rival Sonic. Nor someone powerful like Blaze or Silver. No, he's defeated by the "3 Stooges" because of his own ego.
I think that moment would give Shadow a slice of humble pie he definitely needs. It would also jump start his writing to be more in line to how he used to be.
Being confident, but not outright arrogant.
Also it would be nice to see Team Dark have a newfound respect for Team Chaotix after this.