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I wonder which case the gerund or infinitive is (more) appropriate here: "I did my best to do something" or "I did my best doing something"?

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Your first example is idiomatic.

I did my best to do this. ... It means “I tried as hard as I could to accomplish this”—regardless of whether you actually did accomplish it.

Your second example is not idiomatic, but it is very close to a different idiom.

I did my best in doing this. ... It means “This was the best work I had ever done”—you achieved a new level of excellence.

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    Right. Do one's best to VP is idiomatic and means 'try (hard) to VP', but, like try, it does not imply that one actually succeeded in VP-ing. Do one's best VP-ing, on the other hand, is compositional and merely means 'do one's best while/during/in VP-ing', and it does imply that one succeeded in VP-ing, and did rather well, in fact. Jan 19, 2014 at 17:39

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