Winning as a captain? (5)
I believe the answer is:
ahead
'winning' is the definition.
(I've seen this before)
'a captain?' is the wordplay.
'captain?' becomes 'head' (captaining is a kind of heading).
'a'+'head'='AHEAD'
'as' is the link.
(Other definitions for ahead that I've seen before include "In the lead, in advance" , "In front as in race" , "in van" , "In the future" , "In the leading position" .)