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Taking someone on and winning (8)

Ross

I believe the answer is:

engaging

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'winning' is the definition.
(I've seen this before)

I don't understand the remainder of the clue.

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(Other definitions for engaging that I've seen before include "Taking into employment" , "Attractive or charming - getting married?" , "Attractive; employing" , "embarking on military action" , "Interesting" .)

I've seen this clue in The Guardian and The Globe and Mail.
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