One failing to win quirky roles (5)
I believe the answer is:
loser
'one failing to win' is the definition.
'quirky roles' is the wordplay.
'quirky' indicates an anagram.
'roles' with letters rearranged gives 'LOSER'.
(Other definitions for loser that I've seen before include "Washout" , "Winner's opponent" , "Generally inept" , "One mislaying" , "One failing regularly" .)