Against Red Hood, Green Arrow, Red Arrow, and Starfire
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Lets get it right, Cheshire WAS no joke through the wolfman and perez era when she was a legitimate team buster able to take on high tiers, due to exceptional planning and preparedness.
She was very much made a joke by $#!+ writting in the 90s. She made a little bit of a comeback.
Classic Cheshire takes 7/10
90's Cheshire goes the other way she looses 7/10
Modern, I'd say its a split.
Cheshire in the red hood and the outlaws scans had very different abilities than normal. She could teleport and turn intangible in some kind of green mist form. Those scans don't mean much here.
BW wins here, starting distance favors here guns and stings before Cheshire can do anything with poisons. BW has a lot of experience beating Viper.