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All answers having "Distressing" as clue:

4 Character Answers:

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SORE



5 Character Answers:

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ERROR



6 Character Answers:

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SEVERE



7 Character Answers:

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HURTFUL

PAINFUL



8 Character Answers:

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GRIEVOUS

TERRIBLE



9 Character Answers:

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HARROWING

UPSETTING



10 Character Answers:

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LAMENTABLE