Cryptic crossword clue
Old-fashioned punishment could get contrary English pupil working hard 5

The most common and most likely answer to this crossword clue is the 5 letter word TAWSE

I've seen this crossword clue in The Daily Telegraph
T
A
W
S
E

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The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.
This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.

What does TAWSE mean?

TAWSE noun
  1. A leather strap or thong which is split into (typically three) tails, used for corporal punishment in schools, applied to the palm of the hands or buttocks.
TAWSE verb
  1. To beat with a tawse.

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