n. supervisory responsibility (from OED)
n. the act of passing something over through negligence (also from the OED)
I was ready to close my small run of auto-antonyms when Jonathan Cane suggested this one. It is a wonderful word with two vastly opposing meanings, but one that can almost always be understood by context. It comes from result of forming a compound with a preposition. These often can result in too perfectly reasonable but different meanings.
I’m not sure if this would be a pure contranym because the two phrases don’t necessarily oppose each other. Someone in charge of oversight could easily make an oversight, but the two ideas clearly don’t suit up for the same team.
Interestingly enough, the two different meanings are relatively equal in age according to the O.E.D. As early as 1413, people were using the phrase to mean supervision (which is the exact same word if you think of it). By 1477, it was already used to mean something that was missed.
Oddly enough, oversight can also be used as a verb. One can oversight something by being negligent. It was used in the 1600s, but has still been used in the twenty-first century.
As for Jonathan Cane, when he is not reading my blog, he is training people to run. Check out his website at Citycoach Multisport if you are looking for a coach or if you just want to hear about how he looks good in moose antlers.