Crossword Genius

Most unpleasant defeat (5)

Ross

I believe the answer is:

worst

I believe this clue is a double definition.

'most unpleasant' is the first definition.
('worst' can be similar in meaning to 'most unpleasant')

'defeat' is the second definition.
(worsting is a kind of defeating)

(Other definitions for worst that I've seen before include "Least competent" , "Least well" , "Most inferior or evil" , "Far from the best - defeat" , "The least favorable" .)

I've seen this clue in The Telegraph.
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