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If Task is fast enough.....he takes it.

What do you mean fast enough?

Taskmaster has taken on Spider-Man many times and proven to Spider-Man that speed doesn't mean a damn thing. I'd say he has the most experience when it comes to dealing with Spider-Man in H2H combat considering in most of their encounters Taskmaster has come out on top.

This match would depend on equipment more than anything. Does Taskmaster get "standard" equipment, is this Taskmaster from his miniseries and is this Iron Spider or standard?

Task from Youngbloods

I'm sorry who?