The toff suffered when prevented from winning (7)

I believe the answer is:

nobbled

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'prevented from winning' is the definition.
I can't tell whether this definition defines the answer.

'the toff suffered' is the wordplay.
'the toff' becomes 'nob' (UK slang for a wealthy or upper-class person).
'suffered' becomes 'bled' (I can't explain this - if you can you should give a lot more credence to this answer).
'nob'+'bled'='NOBBLED'

'when' is the link.

Can you help me to learn more?

(Other definitions for nobbled that I've seen before include "Swindled" , "Got at" .)

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