Each winning (5)
I believe the answer is:
ahead
This clue is a double definition.
'each' is the first definition.
('a head' can mean 'per person')
'winning' is the second definition.
(both can mean in the lead)
(Other definitions for ahead that I've seen before include "in van" , "at pole" , "In the leading position" , "What's down the road" , "Winning" .)