Technically the Flash will win. Superman may have super speed, but he has other powers to. Correct me if I'm wrong, but I do believe it was proven in the comics that the Flash is faster. Just my two sense.
Composite picture of every Superman (unsurprisingly) has a sick chin
Here's a cool composite photo that combines the faces of almost every actor that has played Superman. The actors included are Christopher Reeve, Dean Cain, Tom Welling, Brandon Routh, and Henry Cavill.