A win? Encore! (5)
I believe the answer is:
again
'encore' is the definition.
(thesaurus)
'a win?' is the wordplay.
'win?' becomes 'gain' (win is a kind of gain**).
'a'+'gain'='AGAIN'
(Other definitions for again that I've seen before include "Moreover - a second time" , "Repeatedly" , "One more time, encore" , "Furthermore" , "Anew" .)