| 1492 sailer | 11 |
| 1492 ship | 9 |
| 1492 ship of note | 17 |
| 1492 trio member | 16 |
| 1492 vessel | 11 |
| 1492 voyager | 12 |
| 1492, 1776, 2001, etc. | 22 |
| 1492, e.g. | 10 |
| 1493 Columbus landing site | 26 |
| 1499 marble masterpiece | 23 |
| 1499 stop for Amerigo Vespucci | 30 |
| 14A + 6A | 8 |
| 14th anniversary gift | 21 |
| 14th century musical style | 26 |
| 14th century year | 17 |
| 14th Hebrew letter | 18 |
| 14th of Adar | 12 |
| 14th president | 14 |
| 14th U.S. president | 19 |
| 14th-16th century empire | 24 |
| 14th-anniversary gift | 21 |
| 14th-century Bavarian Duke | 26 |
| 14th-century European musical style | 35 |
| 14th-century Florentine exile | 29 |
| 14th-century king of Aragon | 27 |
| 14th-century Russian prince | 27 |
| 14th-century Russian ruler | 26 |
| 14th-century Russian ruler called "the Moneybag" | 58 |
| 14th/15th-century period of papal uncertainty | 45 |
| 15 before the hour | 18 |
| 15 mg. of zinc, e.g. | 20 |
| 15 miles of it are mentioned in a song | 38 |
| 15 miles of song | 16 |
| 15 min. of football | 19 |
| 15 min. on the gridiron | 23 |
| 15 MINUTES | 10 |
| 15 minutes of tightrope walking and animal acts? | 48 |
| 15 OUNCES | 9 |
| 15 per cent of the check | 24 |
| 15 percent of a bill, perhaps | 29 |
| 15 preceder | 11 |
| 15 slices, maybe | 16 |
| 15 years before Hastings | 24 |
| 15 years before the Battle of Hastings | 38 |
| 15 ___ (tennis score) | 21 |
| 15% usually | 12 |
| 15% of MMM | 10 |
| 15% of the tab, usually | 23 |
| 15%, maybe | 10 |
| 15%, often | 10 |
| 15%-20%, for a waiter | 21 |
| 15%-20%, usually | 16 |
| 15%-er: Abbr. | 13 |
| 15, 30, 45, ___ | 15 |
| 15, for any row, column or diagonal of a 3x3 magic square | 57 |
| 15-0 in baseball, e.g. | 22 |
| 15-15 or 40-40 | 14 |
| 15-21-13-1-18-6 | 15 |
| 15-ball cluster | 15 |
| 15-minute CDs | 13 |
| 15-ml unit | 10 |
| 15-percenter | 12 |
| 15-percenter: Abbr. | 19 |
| 15-percenters: Abbr. | 20 |
| 15-time N.B.A. All-Star who announced his retirement on Twitter | 63 |
| 15-time NBA All-Star Kevin | 26 |
| 15-time Primetime Emmy nominee | 30 |
| 15-year-old, legally | 20 |
| 15.432 grains | 13 |
| 15.4324 grains troy | 19 |
| 150 followers of Job | 20 |
| 150 followers of Job? | 21 |
| 150 percent of due | 18 |
| 150% of due | 11 |
| 150-miles-per-hour Amtrak train | 31 |
| 1500 | 4 |
| 1500-meter winner at the 1964 Olympics | 38 |
| 1500-mile river to the Caspian Sea | 34 |
| 1500s painter known for his "Lives" of Italian artists | 64 |
| 1501 in Roma | 12 |
| 1501, in ancient Rome | 21 |
| 1501, in old Europe | 19 |
| 1501, in Roman numerals | 23 |
| 1501, on a monument | 19 |
| 1501, to Caesar | 15 |
| 1501, to Nero | 13 |
| 1502, on a monument | 19 |
| 1502, on monuments | 18 |
| 1502, to Caesar | 15 |
| 1504, to Caesar | 15 |
| 1506, in Roman numerals | 23 |
| 1507 masterpiece | 16 |
| 151 in old Rome | 15 |
| 151 on a monument | 17 |
| 151 to Big Julie | 16 |
| 151, in old Rome | 16 |
| 151, in Roman numerals | 22 |
| 151, on a monument | 18 |
| 151, to Caesar | 14 |
| 151, to Cato | 12 |