The thread should be restated to ask "who doesn't surpass there masters" as most everyone does save a few exceptions who in one way or another have technically surpassed there masters if not matched them.
All in all i think the younger generation will always surpass the older because it is the older that are teaching the younger generation, for the younger generation not to surpass the older wouldn't that mean the older generation has failed as teachers? It doesn't take much to become a great ninja, all you need is a large chakra pool(which you are born with), a bloodline limit doesn't hurt, good taijutsu skills which the older generation teach you and jutsu's which you also get from the older generation, as a matter of fact one could say it is impossible for the younger generation not to surpass the older generation. It would be like asking whether today's scientist would ever be able to surpass the older scientist like Albert Einstein. I mean you can argue how Einstein was a genius and how he was one of a kind, but the newer generations of scientist have taken what he originally did and built on it making it there own and unique to them, and we see that Einstien was merely the foundation on which we could see smarter and better scientist build upon. We see the trend everywhere, people and civilizations progressing with time and not the other way around.
You ask whether or not the student can surpass the master, my answer is simple... its inevitable.
Below is a little farfetched theory on this, I wont try to hard to defend this as I know I probably made alot of mistakes but by chance I might make a point ill.
To pry at this a little further, I can see how someone can be mistaken to think the older generation is stronger than the younger. I mean look at Madara who took on all 5 kages calling them weak and he was nothing compared to hashirama. We see this illusory trend of the older generations being stronger than he younger. But one thing we should keep in mind is that Obito and Hashirama arent really human. They are genetic freaks strung together by Hashirama's DNA. To get an actual gauge of there strenght lets compare a few things. Hashirama was stronger than Madara. Hiruzen at his prime was as strong if not stronger than Hashirama. Orochimaru beat old man Hiruzen, it can be said that Hiruzen was an old man but it also could be said that Orochimaru was toying around with him summoning the old hokage to mess with him, he underestimated him and lost his arms but toyed with him non the less. So at this point we can draw a connection between Hashirama's power and Orochimaru with oro being slightly weaker ofcourse, not to be a fanboy but im just following the facts. From this point on we can simply compare Oro to others and see how that stacks up, remember that Oro is pretty strong taking on 2 sannin without his arms or the ability to use any jutsu(which means all he has is taijutsu) it should also be noted that he took a pounding from Tsunade at full power and shrugged it off, both of which are hokage level.
So now we have to ask, who at this point can compare to Oro. Naruto easily, probably sasuke as well. Danzo as he could have beaten sasuke if it was a 1v1, 3rd raikage possibly, gaara and a few more. With that we can see that there are alot of people in the manga during the 5kage timeline through to the shinobi war timeline that are close to hashirama's level, if not already there as we dont know how a battle between the 2 would turn out.
Just be sure not to take overpowered madara too seriously right now as he is basically Madara + hashirama, has practically unlimited chakra, infinite stamina courtesy of the edo tensie jutsu, rinnegan courtesy of Hashirama cells, and on top of that we havent really seen him do much. Just shadow clones with susano's and alot of big talk.
