'winner' has a single value constraint with some separators. It can be used as a qualifier. But if there are multiple values as qualifiers, the separators cannot be used. The suggestion "This property should only have a single value with the same set of qualifiers..." is then quite useless. Perhaps it could be reworded.
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Should we switch the violation message to the version without separators if we’re not checking the main statement? Or should the check be done differently?
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I think that the violation message should be shown only if the property is used as main value, not when it is used as qualifier (see also https://www.wikidata.org/wiki/Q830798#P8189).
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You can change that for an individual constraint with the constraint scope constraint parameter.