Well, I think both are comparable in stats with Kagura being around 2.2GT while Cracker is around 2.6GT, giving a little power advantage. That and the army Cracker can create just clapping will give lots of problems to Kagura.
The main disadvantage for Cracker is that he'd panic really fast if he gets a cut, no matter how little it is, affecting his mindset and making him prone to fight bad and fail in the most simple things. This is something Kagura can easily exploit with her unique fighting style, that could help to outmaneuver the Biscuit Soldiers. Since she has a sword she could cut through them easier, considering cutting something is easier than breaking it with blunt force like Luffy did.
If it comes to a physical contest, Cracker has more advantages with his slightly superior stats, with Class G pushing harder than Class M, and the possibility to increase his stats even more with Haki.
Kagura could dodge the Biscuit Soldiers or try to take them down, but if she doesn't take Cracker down this will end bad for her.
If Kagura manages to land a clear cut on Cracker before he can spam his army, then she'd have more opportunities, but Cracker uses the first Biscuit Soldier as an armor that protects him, and IIRC, the shields were able to take G4 punches directly.
So, as much as my heart hurts, Cracker should take his first win. He's better stats, better field game and the possibility to win the endurance game since Kagura will lose his magic power faster than Cracker will get tired.
I want OP to win but not against Kagura SOAPW
Edit: Someone tell me I'm wrong here. Please.