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This isn't a traditional match, per se.

Basically, I've chosen 4 matches each from both movies. The twist is that Ip will take Huo's place in the Fearless matches (weapons for specific matches) and Huo will fight in Ip's place in the Ip Man matches.

For Fearless:
1. Tiger Claw Dude
2. Master Qin*
3. Hercules O'Brien
4. The Boxer, The Spearman, The Fencer, and Tanaka (no poison)*

For Ip Man:
1. The Northerner*
2. 12 black belts
3. The Northerner (rematch)*
4. General Miura

* means weapons enabled. Huo has his sword and three part staff and Ip got his staff and duster.

Which Chinese legend will clear this match?

To be honest. They'd probably split a lot of them 5/5. Both Huo, and Ip were legends in their own right.

Yeah, putting them up against each others opponents only allows them to show more of their badassery...and gets 10 people 10 new and unique beatdowns.