I already posted this on math.stackexchange, but I'm also posting it here because I think that it might get more and better answers here! Hope this is okay.
We all know that problems from, for example, the IMO and the Putnam competition can sometimes have lovely connections to "deeper parts of mathematics". I would want to see such problems here which you like, and, that you would all add the connection it has.
Stanislav Smirnov mentions the following from the 27th IMO: "To each vertex of a regular pentagon an integer is assigned in such a way that the sum of all five numbers is positive. If three consecutive vertices are assigned the numbers $x,y,z$ respectively, and $y <0$, then the following operation is allowed: the numbers $x,y,z$ are replaced by $x+y$, $-y$, $z+y$, respectively. Such an operation is performed repeatedly as long as at least one of the five numbers is negative. Determine whether this procedure necessarily comes to an end after a finite number of steps".
He mentions that a version of this problem is used to prove the Kottwitz-Rapoport conjecture in algebra(!). Further, a version of this has appeared in at least a dozen research papers.
(Taken from Gerry Myerson in this thread http://math.stackexchange.com/questions/33109/contest-problems-with-connections-to-deeper-mathematics)
On the 1971 Putnam, there was a question, show that if $n^c$ is an integer for $n=2,3,4$,… then $c$ is an integer.
If you try to improve on this by proving that if $2^c$, $3^c$, and $5^c$ are integers then $c$ is an integer, you find that the proof depends on a very deep result called The Six Exponentials Theorem.
And if you try to improve further by showing that if $2^c$ and $3^c$ are integers then $c$ is an integer, well, that's generally believed to be true, but it hadn't been proved in 1971, and I think it's still unproved.
The most interesting part would be to see solutions to these problems using both elementary methods, and also with the more abstract "deeper methods".