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In this sentence, which word is more suitable:

I'll think of you as we watch the Blue Socks win/winning the game.

Any help about the grammar here would also be appreciated.

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The actual meaning of your sentence is

I'll think of you as we watch the the game involving the Blue Socks, which I am confident (even certain) they will win.

It would be very difficult to watch just the "winning" of the game. Would that be the instant that the clock runs out, or the last scoring play, or the moment at which the Blue Socks first went ahead on the score board?

So this is a type of telegram or shorthand sentence that is common in spoken conversation (or texting) but is very difficult to push into the conventions of formal writing.

When used to taunt your friend who supports the (known to be hopeless) Red Caps, feel free to use either form.

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If the speaker is assuming that the Blue Caps will take an early lead and hold onto it, winning could be an appropriate word. If the speaker is alluding to the end result, though – those final moments of the game when the clock runs out, or the last outs are made – then win could be the better choice. – J.R. Jul 5 '13 at 10:07

Grammatically both are correct and suitable.

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Shaona, so "win" and "winning" have the same meaning even when they are used in different contexts, and, eventually, @Fortiter's answer is wrong? – user19148 Jul 5 '13 at 11:05
@Carlo_R. Of course not. Only in this context both are correct. – Shaona Bose Jul 5 '13 at 12:35

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