I don't know much about Bockwinkle, but a little bit of research was all that was needed to tell me that he was a phenomenal talent. Shane McMahon has the reputation of a spot monkey, and indeed some of his most memorable moments come from taking ridiculous bumps in a Mick Foley fashion. This match is difficult to call, as I've been trying to look at this match from an objective point of view. Shane tends to work his best in a hardcore setting, and considering that this match is a no Disqualification, that gives Bockwinkle the advantage. Shane can hold his own against technical wrestlers, based on his durability and longevity alone, the only problem is that he can only go so hard for so long, hence the reason why he flourishes in a hardcore environment, to nullify his opponent's superior strength and/or technique. Without that hardcore environment to fall back on I see Bockwinkle picking Shane apart.
Winner Bockwinkle