F-14s would have no problem detecting a low flying plane. The AWG-9 is a doppler radar system, in laymans terms it means it sees that which moves, so it would see the planes even at sea level (unless they were flying through a storm with 20 foot waves of course, but I suppose no one is crazy enough to try)


Whoever was defending would win.
A defending air-force will always have the advantage of more fuel and help from integrated air defense, etc.