Fight on an abandoned building site.
In character, but ready to kill
No prep
Fight to the death
Round 1: Stark vs Optimus Prime, Tony doesn't have an armor and is armed with a chainsaw and a katana, Optimus before getting improvements (first movie version)
Round 2: Tony has access to his armor he used in Avengers, and he has Daredevil and Charles Xavier helping him (movie versions as well). Daredevil is armed with his billy clubs, Xavier is in wheelchair, has no mutant powers and wields his steel sledgehammer. They fight against Optimus, Megatron, Galvatron and Lockdown (all in their prime)
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