Cryptic crossword clue
Worked painfully hard to ruin rival date 9

The most common and most likely answer to this crossword clue is the 9 letter word TRAVAILED

I've seen this crossword clue in Independent
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Buddy explains!

The straight part
We know that "Worked painfully hard" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case worked painfully hard = travailed.
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 TRAVAILED mean?

TRAVAILED verb
  1. To toil.
  2. To go through the labor of childbirth.

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