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The Hindu Crossword 6631 (1st Jan 2000)
Starting off with the earliest crossword puzzle I had found, back from 1st Jan 2000. This was crossword number 6631 when it was originally published. For those who are interested or curious, there was a "special" post on the hindu crossword corner blog that featured this same crossword puzzle. That blog has also featured a few more old ones (like crossword no. 6632), but does not have too many old puzzles as far as I can tell. Unfortunately, I do not have information about the setter, nor do I have the answers to this puzzle. If you have more details, please leave them in the comments, and I can update this post with more details.
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