Iron Man may have underestimated Whiplash a bit:

I hadn't planned on turning this into Whiplash Week, but I ended up with a highlight reel of his gimp mask appearances. He doesn't make too bad of a showing for himself.

Sometimes, if you face the same opponent over and over, whether in basketball or chess or fighting, you can feel pretty strongly that you have their number. That you know every move they've got, and that you've got it over them. Until they step it up. Maybe they pick up a weak spot in their game--like mobility, which Whiplash improves with a flying disc and later boot-jet things--or pick up some new technique--like Whiplash's new arsenal of whips, with varied effects. Or maybe, they just really want to beat you now.

Although one of these was a dream sequence, Iron Man doesn't beat Whiplash in any of these issues. Closest he comes is a draw, and he came out the worse in that one even. Of course, there's still the matter of Whiplash's death, which hopefully I'll get to before I go on vacation.

Panels from Iron Man #11, "Schedule Conflicts" Written by Kurt Busiek, pencils by Sean Chen, inks by Larry Strucker and Eric Cannon; Iron Man #8, "The Hunt" by Busiek, Chen, Cannon and Sean Parsons; Iron Man '99 Annual, "Power Tools" Co-plotted by Busiek, plot and script by Joe Casey, pencils by Terry Shoemaker, inks by Bud LaRosa and Shoemaker; and Iron Man #26, "The Mask in the Iron Man, part one" Written by Joe Quesada, pencils by Chen, inks by Rob Hunter.