Crossword clues for the word: MIDDLESEX The word MIDDLESEX has appeared as an answer to at least 6 crossword clues on different crossword puzzles. Crossword clues for MIDDLESEX Showing 1 to 6 of 6 results Clue(s) "County in Conn., Mass., N.J.or Va." 2002 novel by Jeffrey Eugenides 2003 Jeffrey Eugenides Pulitzer Prize-winning novel about a hermaphrodite Connecticut county New Brunswick's county Where Tottenham is.