Does he hope to ride a record winner? (4,6)
I believe the answer is:
disc jockey
'does he hope to ride a' is the definition.
The answer is a person as well as being a singular noun. This is suggested by the definition.
'record winner?' is the wordplay.
'record' becomes 'disc' (eg a CD, compact disc).
'winner?' becomes 'jockey' (I am not sure about this - if you are sure you should give a lot more credence to this answer).
'disc'+'jockey'='DISC-JOCKEY'
Can you help me to learn more?
(Other definitions for disc jockey that I've seen before include "Pop music presenter" , "Radio presenter of pop records" , "Radio player of popular music" .)