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The verb "ganar" means more than just "to win". It can mean "to beat", "to earn" and "to gain" and lots of other things when joined with other words. It's just down to picking the most suitable word for the sentence. In this case, "He can BEAT me" seems the most obvious choice. I honestly don't know how...if in some strange situation, you were a raffle prize, you would say "He can win me", hopefully someone can let us know.
Maybe you would have to say "Él me puede ganar como un premio", to clarify things. I just don't know.
in english "to win someone" can mean , yes, you were a raffle prize, or an auction-date, but it can also be used in the sense to sway someones opinion so that they agree with you. Is this verb an appropriate parallel for this type of meaning, perhaps duo has forgotten to include for this?
Indirect object pronouns can go in two places - before a conjugated verb, or attached to the end of the infinitive.
Me puede ganar
Puede me ganar
I've heard that the difference between Me puede ganar and Puede ganarme is mostly just a choice in style, and sometimes placing the indirect object can help give clarity. But the meaning doesn't change if it's attached to the end of an infinitive vs. before a conjugated verb.