| 14 pounds, across the pond | 26 |
| 14-line, two-rhyme poem | 23 |
| 14-time All-Star Rodriguez | 26 |
| 140 characters-or-less posts | 28 |
| 140 pounds to a Londoner | 24 |
| 140 pounds, in Britain | 22 |
| 1492 Columbus discovery | 23 |
| 1492, 1776, 2001, etc. | 22 |
| 1493 Columbus landing site | 26 |
| 1499 marble masterpiece | 23 |
| 14th century musical style | 26 |
| 14th-16th century empire | 24 |
| 14th-century Bavarian Duke | 26 |
| 14th-century Florentine exile | 29 |
| 14th-century king of Aragon | 27 |
| 14th-century Russian prince | 27 |
| 14th-century Russian ruler | 26 |
| 15 min. on the gridiron | 23 |
| 15 per cent of the check | 24 |
| 15 percent of a bill, perhaps | 29 |
| 15 years before Hastings | 24 |
| 15% of the tab, usually | 23 |
| 15-0 in baseball, e.g. | 22 |
| 15-time NBA All-Star Kevin | 26 |
| 1501, in Roman numerals | 23 |
| 1506, in Roman numerals | 23 |
| 151, in Roman numerals | 22 |
| 1519 Yucatán arrival | 23 |
| 152, in Roman numerals | 22 |
| 1521 stop for Magellan | 22 |
| 155, in Roman numerals | 22 |
| 1552, on a cornerstone | 22 |
| 1558-1603 monarch: Abbr. | 24 |
| 157.5 degrees, to a pilot | 25 |
| 157.5° to a mariner | 22 |
| 15th state to join the Union | 28 |
| 15th-century fleet member | 25 |
| 15th-century Flemish painter | 28 |
| 15th-century imperialist | 24 |
| 15th-century king of France | 27 |
| 15th-century maritime name | 26 |
| 16 and Seventeen, for short | 27 |
| 16 or Seventeen, for short | 26 |
| 16-1 baseball score, e.g. | 25 |
| 16-symbol system, for short | 27 |
| 16-time medalist Michael | 24 |
| 16-year-old's desire | 24 |
| 16-year-old's want | 22 |
| 16-year-old, typically | 22 |
| 1600 Pennsylvania Ave., e.g. | 28 |
| 1600 to 1800, on a boat | 23 |
| 164-foot-tall movie star | 24 |
| 1650, in Roman numerals | 23 |
| 1655 conqueror of New Sweden | 28 |
| 1666 London fire chronicler | 27 |
| 1669 Louis Jolliet discovery | 28 |
| 1669 sight for Louis Jolliet | 28 |
| 1676 Virginia uprising | 22 |
| 1692 witch trials city | 22 |
| 1692 witch trials setting | 25 |
| 16th C. ecumenical council | 26 |
| 16th century council site | 25 |
| 16th century dramatist Thomas | 29 |
| 16th century Italian poet | 25 |
| 16th century painter Veronese | 29 |
| 16th century's end | 22 |
| 16th letters in Hebrew | 22 |
| 16th president familiarly | 26 |
| 16th president's nickname | 29 |
| 16th president, familiarly | 26 |
| 16th president, informally | 26 |
| 16th-century artist Veronese | 28 |
| 16th-century circumnavigator | 28 |
| 16th-century council city | 25 |
| 16th-century council site | 25 |
| 16th-century Florentine food? | 29 |
| 16th-century Italian sculptor | 29 |
| 16th-century Spain, for one | 27 |
| 16th-century Spanish explorer | 29 |
| 16th-century Spanish fleet | 26 |
| 16th-century Spanish mystic | 27 |
| 17 1/2 million square miles | 27 |
| 17-1 baseball score, e.g. | 25 |
| 17-mission NASA program | 23 |
| 17-mission space program | 24 |
| 17-syllable form of poetry | 26 |
| 17-syllable verse form | 22 |
| 1740 Samuel Richardson novel | 28 |
| 1751 Henry Fielding novel | 25 |
| 1773 Boston Harbor jetsam | 25 |
| 1773 jetsam in Boston Harbor | 28 |
| 1775 foe of the British | 23 |
| 1776 and 2001, e.g.: Abbr. | 26 |
| 1777 Pennsylvania battle site | 29 |
| 1778 visitor to Hawaii | 22 |
| 1786 rebellion's eponym | 27 |
| 1788 stop for the Bounty | 24 |
| 1790s diplomatic powder keg | 27 |
| 1794 patent awardee Whitney | 27 |
| 1796 Napoleon battle site | 25 |