From this page (for example) we can get some idea of the way oak root systems grow. First the tap root goes down, then horizontal roots are established. If you examine the roots in the pots likely you will find a thickish main root which will hit the bottom of the pot and then go round in a circle at the edge of the pot. It wants to go down further but cannot. To keep them in a container would produce a bonsai plant, which requires quite a bit of work.
Ideally we want to gently tease that tap root away from the base so that it hangs in a sort of coil downwards, but not loosen the actual root ball. Then the waiting hole in the ground will be deep enough to accommodate that tap root to its full length. Back fill the hole around the tap root leaving the main root ball at ground level. When you remove from the pot make sure that the root ball is moist so that it hangs together without falling apart, and transplant on a cool still day to prevent the root from drying out.
Thinking ahead, make sure that it is you that interferes with the roots on planting. Then you are able to take full responsibility for the event that one survives and not the other. It must have been me, I'm sorry.