Hmm. A thought occurs.
In canon, Goku was able to match jackie chun, for the most part, and Kakarot is a fair bit stronger. Thus, ordinarily, I'd predict that chun loses this one. But. That's not exactly the case, is it?
Rather, Goku was losing flat out to jacki, and only pulled out a close finish after oozaroo let him break free of the lightning and then forced chun to waste a ton of power destroying the moon. Kakarot, for all his extra skills, doesn't have anything to beat lightning, and since he's facing Chun in semifinals and not finals he doesn't have oozaroo as a get out of jail free card.
Thus, calling it now:
Chichi beats yamcha. It's closer than she expects, because he has some tricks, but ultimately she's just plain stronger than him.
After a long battle where both pull out all the stops, Kakarot loses to Chun. Gine almost loses her shit, but the fact that Kakarot is, technically, fine is enough to barely restrain her from going all out. She may or may not partly out herself in the process, still unsure on that predicition but its definitely a possibility.
Chichi vs Jackie Chun, highlight match. Chichi has seen all of Roshi's tricks, and he may not have fully recovered, but at the same time she's not quite as good as Kakarot and she shares some of the same tricks as he does, which roshi will also be familiar with. Ends in a Chichi victory, possibly with oozaroo interference.
Krillin has more self esteem issues to get over, poor kid. Good odds that he's the one who ends up receiving training from korrin first, at least.