What Dan Henderson brings to the table: Henderson is a legend in MMA for a reason. First, he has awesome wrestling skills, allowing him to usually dictate where fights will take place. Second, he has a great jaw and is very hard to submit. Last, Henderson possesses solid technical striking skills and hits like a truck.
In terms of weaknesses, he doesn't tend to have too much in the line of submissions. Further, he sometimes gets caught up standing with people when the smart money says he should just be taking them down.
What Michael Bisping brings to the table: Michael Bisping is a former TUF Champion that possesses excellent technical Muay Thai kickboxing skills and submission skills. He's also very tough and always comes to fight in shape. Having recently dropped down to the middleweight division from the light heavyweight class has allowed him to gain some power over his opponents.
That said, Bisping's relative weakness would appear to be his wrestling. He's gotten much better with his takedown defense, etc., but his wrestling skills are not at the level of his other capabilities.
Dan Henderson vs. Michael Bisping Prediction: Bisping has diverse striking skills that could give Henderson some level of trouble. That said, Henderson's legendary toughness and jaw should keep him out of any grave danger on his feet. Further, if he fights the smart fight, he'll look to take his adversary down and pound away at him early on. Guess is that Bisping will eventually become so concerned about getting taken down that it will take away from his striking skills to the point that Henderson will land a big shot. That plus the wear and tear of the likely ground and pound he'll be receiving should spell trouble for the British fighter.
Dan Henderson wins by TKO in round three.

