Most uncomfortable match.

I’m thinking along the lines of Rock vs Mankind from the Royal rumble 99 and watching the numerous unprotected chair shots to the head. Another strong contender would be Austin vs Michaels at WM 14 just knowing and being able to clearly see how much pain Shawn was in.

A dark horse contender for me would be Eddie vs Rey in a ladder match at SummerSlam 2005. Besides Eddie getting very noticeably angry at Vickie for missing her cue he just looked angry and very unhealthy or worn down by injuries the entire match. Of course he passed away a couple of months later which adds to it.

Any matches stand out for you?