Redgrave perhaps initially receives Oscar with sign of hesitation (5)
I believe the answer is:
rower
'redgrave perhaps' is the definition.
(Steve Redgrave is an Olympic rower)
'initially receives oscar with sign of hesitation' is the wordplay.
'initially' indicates taking the first letters.
'sign of hesitation' becomes 'er'.
The first letters of 'receives oscar with' is 'row'.
'row'+'er'='ROWER'
(Other definitions for rower that I've seen before include "Oarsman/woman" , "Oarsman (or woman)" , "Stroke with blade" , "Maybe one in eight" , "one pulling a blade?" .)