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This is just after Ippo's first arc, when he narrowly beats Takeshi Sendou the first time.

Takamura, bored without anyone to fight, decides to spread some rumors that Ippo is full of himself after his wins, and was talking shit about being able to beat Aoki and Kimura at the same time. So the two confront Ippo, and while he's trying to figure out what's going on, Takamura escalates things until a sparring match is set up, with him as the ref.

1. Ippo vs Aoki

2. Vs Kimura

3 rounds each, all out, no rest between match's.

Ippo stomps hard. Aoki is fodder and Kimura is a choke artist.

Wait, you said this is after his first fight with Sendou. Hmm. Yeah, it's been a while since I've read the manga, but Aoki and Kimura weren't joke characters at that point, were they?

At that point, against both, Ippo would get some good hits in, but he would lose. By then I don't think he'd seen their true fighting styles yet, and didn't realize that they were actually decent fighters who weren't better because they relied on gimmicks instead of just balls to the wall training all the time like him and Takamura.

Ippo could beat both individually but together her just doesn't have the talent to take on two guys at once. That shit is hard to do. There is a moment way later in the manga where Takamura tries to be badass and take on three opponents at once without getting touched. He knocks one guy out no problem but then one of the others just hits him in the face. He still wins obviously but if Takamura doesn't have the spacial awareness to track more than one opponent, Ippo surely doesn't lol.

Edit: Oh it's a gauntlet. Unless Kimura is 100% on his A game then Ippo would win. Aoki hasn't mastered "that technique" yet and I don't think Kimura has had his big moments either.