I'm aware of precisely one word that is spelled and pronounced the same, yet has a completely opposite meaning depending on its context: sanction.

On one hand, it is official permission for something.

On the other hand, it is a penalty (so, the opposite of permission).

Yet you could sanction (give permission for) a sanction (penalty to be applied). Hm.

Are there any other homonyms that share this trait of having directly opposing meanings?

  • 2
    Yes, at least a few. Look around and tell us what you found! Good Luck.
    – Kris
    Dec 11 '18 at 7:11

These words are called auto-antonyms or contronyms; Wikipedia has an extensive list of examples in the English language, including your 'sanction'.

My favourite is 'oversight':

"Oversight" can mean "accidental omission or error", or "close scrutiny and control".

since they (too) often occur together...

  • That was exactly what I was looking for - wasn't aware of the precise term for this.
    – Mikey T.K.
    Dec 12 '18 at 16:54

There are no homonyms, synonyms, homographs, none.

It's a Janus word, a type of polysemy, more precisely, "auto-antonymy (WP)."

An auto-antonym or autantonym, also called a contronym or contranym,[2] is a word with multiple meanings (senses) of which one is the reverse of another. For example, the word cleave can mean "to cut apart" or "to bind together". This phenomenon is called enantiosemy,[3][4] enantionymy or antilogy (enantio- means "opposite"). An enantiosemic term is necessarily polysemic.

antagonym, enantiodrome, self-antonym, antilogy, or addad (Arabic, singular didd).

"Draw" the curtains can mean either to open them or to close them.
"Dust" can mean to remove dust (cleaning a house) or to add dust (e.g. to dust a cake with powdered sugar).

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