Most awkward round cowboy (6)
I believe the answer is:
gaucho
'cowboy' is the definition.
(gaucho is a kind of cowboy)
'most awkward round' is the wordplay.
'most' means to remove the last letter.
'awkward' becomes 'gauche' (I've seen this before).
'round' becomes 'o' (round can mean a round object).
'gauche' with its final letter taken off is 'gauch'.
'gauch'+'o'='GAUCHO'
(Other definitions for gaucho that I've seen before include "Cowboy of Argentine's plains" , "Surprise attacker" , "Ranch hand" , "Horseman of the S American plains" , "A cough (anag)" .)