| 100% | DSIX | 4 | Square in chess and Battleship |
| 44% | KING | 4 | Piece in checkers and chess |
| 44% | DTEN | 4 | Square at the end of the fourth row in Battleship |
| 43% | PIGEONS | 7 | Birds traditionally seen in city squares and parks |
| 43% | STATIONS | 8 | Times Square and Columbus Circle, in New York City |
| 42% | THREE | 5 | Number of squares in the width and height of this puzzle's city blocks |
| 42% | BARRIERSTOENTRY | 15 | Impediments to newcomers, illustrated by black squares in rows 2, 4, 12 and 14 |
| 42% | ACRE | 4 | One of six hundred and forty in a square mile |
| 42% | ANYAS | 5 | Q: ___ / A: Yes, two, in the second and sixth squares |
| 41% | CHECKMATE | 9 | Position in chess where 13d has no escape and the attacking player wins the game |
| 41% | ORIGINSTORES | 12 | The Macy's in New York's Herald Square, and others? |
| 41% | PARTTHEREDSEA | 13 | Emulate Moses ... and what four black squares do in this puzzle |
| 41% | MOVES | 5 | Qxd5 and Be3, in chess notation |
| 40% | FDR | 3 | Pres. that has a memorial and statue in Grosvenor Square, Mayfair, London |
| 40% | DOESITHAVEANN | 13 | Q: ___ / A: There are two, in the third and seventh squares below |
| 40% | AFRAMEBUILDINGS | 15 | Structures illustrated twice in this puzzle through both black squares and letters |
| 39% | SUM | 3 | 34, for each row, column and main diagonal in a 4x4 magic square |
| 39% | FAIR | 4 | ___ and square (in an honest way) |
| 38% | ELLS | 4 | The black square chunk in front of 55-, 60- and 63-Across, and others |
| 38% | WHATIMPLEMENT | 13 | With 28-, 48- and 56-Across, riddle whose answer appears in the circled squares |
| 38% | NEW | 3 | With 65- and 66-Across, when to sing the song in the circled squares |
| 38% | SORT | 4 | Categorize ... and, when read differently, the letters that can go in the circled squares |
| 38% | WARGAMES | 8 | Chess and Risk |
| 38% | SLOANE | 6 | Square in London |
| 38% | PIAZZA | 6 | Square in Rome |
| 38% | UNION | 5 | Square in manhattan |
| 38% | COPLEY | 6 | Square in Boston |
| 38% | TANGRAM | 7 | Chinese puzzle in which a square is cut into seven pieces and formed into figures |
| 37% | SOULCYCLE | 9 | Spin class company ... and what can describe the arrangement of letters in the circled squares? |
| 37% | ZEROSUMGAMES | 12 | Chess and tennis, mathematically |