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I have read the following sentence:

Per mesi stette dietro al mio nemico.

What could "stare dietro" mean here? "to keep an eye on somebody", "to follow", something else ? I have read http://www.treccani.it/vocabolario/dietro_%28Sinonimi-e-Contrari%29/ , but I found several meanings.

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In this phrase, the meaning is the first one you wrote:

Stare dietro (a qualcuno)

means "to keep an eye (on somebody)" or "to watch over (someone)"; this is the meaning reported on the Treccani page you linked:

stare dietro (a qualcuno) ≈ sorvegliare (ø)

The other meaning (i.e. "to follow") can be used for example when you are talking about a chase.

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  • 1) So "stare dietro a" here could not mean that he was physically following my enemy for months to see what he's doing, where he's going, who he's meeting, etc so that I could take advantage of that info in the future? 2) forum.wordreference.com/threads/stare-dietro-a.131384 mentions that two possible translations are "to keep up with" and "to take care" (eg of a child), which I do not see in Treccani. Are those also valid translations in other contexts (eg mia mamma riesce a stare dietro a mia figlia che ha solo 5 anni) ?
    – Alan Evangelista
    Commented Oct 3, 2019 at 16:45
  • @AlanEvangelista More context would perhaps be useful. But the two basically are the same thing, aren't they?.. When you keep an eye on someone, you do follow them.
    – Evgeniy
    Commented Oct 3, 2019 at 18:20
  • @Evgeniy no. A nanny keeps an eye on the children she is taking care, but she does not follow them around. A boss keeps an eye on a lazy employee, but he does not follow him/her. "to keep an eye on somebody" = to be attentive / to pay attention to someone's actions. to follow = to physically follow (eg a detective followed the gangster to find his hideout)
    – Alan Evangelista
    Commented Oct 3, 2019 at 18:25
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    In my opinion, "Stare dietro (a qualcuno)" o "Stare dietro (a qualcosa)" means to actively focus your attention on him/her/it; This is the sense of the phrase about the mommy reported by @AlanEvangelista; you can also use expressions like "Sto dietro al calcio" (= I am interested on soccer)
    – Riccardo De Contardi
    Commented Oct 3, 2019 at 19:31

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