1

He worked very hard but he failed to win the match.

Can I delete the second 'he'?

2

Yes. The subject he will be understood. Where you have two verbs that have the same subject, and want to join them with a conjunction, you put the subject first, then the first verb and any objects and adverbs and so on, then the conjunction (here that is but), and then the second verb with its objects and adverbs.

(Because I'm also a bit of a maths nerd, I think of that as the subject being distributive over the conjunction. No idea if that term is used in linguistics.)

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