oversee and overlook are staples on lists of "contranyms"
[yart alert]. they have arrived in this sorry (but interesting) state through a process of enantiodromia. as to other enantiodromic words, examples have been discussed elsewhere but a somewhat related one is 'peruse'.

I think what actually happens with these is that a particular meaning becomes generalized and then re-particularized in the opposite direction. e.g., with peruse the original meaning was specifically to read with all due attention, then it came to mean just to read, and now is likely meant to convey casual reading without attention to detail.