Not having won, is lamenting troubles (4)

I believe the answer is:

ails

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'troubles' is the definition.
(as verb)

I can't explain the remainder of the clue.

(Other definitions for ails that I've seen before include "Is unwell - sail away" , "Is ill or uneasy - sail away" , "Feels unwell" , "Is sick" , "Troubles; afflicts" .)

I've seen this clue in The Guardian.

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