| 1999 Stanley Cup finals competitor | 34 |
| 1999 Stanley Cup winner | 23 |
| 1999 Steven Soderbergh movie, with "The" | 50 |
| 1999 subject of a tug-of-war | 28 |
| 1999 Sutherland movie | 21 |
| 1999 teammate of Brandi, Briana et al. | 38 |
| 1999 teammate of Brandi, Briana, et al. | 39 |
| 1999 Tim Allen/Sigourney Weaver cult comedy | 43 |
| 1999 title role for Julia | 25 |
| 1999 Tom Cruise movie | 21 |
| 1999 Tom Hanks film, with "The" | 41 |
| 1999 Tony-winning musical | 25 |
| 1999 Top 10 hit for Sixpence None the Richer | 44 |
| 1999 U.S. Open champ | 20 |
| 1999 U.S. Open champ Andre | 26 |
| 1999 U.S. Open winner | 21 |
| 1999 U.S. Open winner Andre | 27 |
| 1999 U.S. Open winner Stewart | 29 |
| 1999 U.S. Ryder Cup team captain | 32 |
| 1999 US Open champ | 18 |
| 1999 war combatant | 18 |
| 1999 war site | 13 |
| 1999 Will Smith movie | 21 |
| 1999 Winona Ryder movie | 23 |
| 1999 Women's World Cup host | 31 |
| 1999 World Series MVP Rivera | 28 |
| 1999 World Series runner-up: Abbr. | 34 |
| 1999 Yankee | 11 |
| 1999 Yankee pitcher | 19 |
| 1999, 2000 and 2001 Best Actor nominee (he won once) | 52 |
| 1999, e.g. | 10 |
| 1999, on Chinese calendars | 26 |
| 1999-2000 "Dame" on Broadway | 38 |
| 1999-2000 name in the news | 26 |
| 1999-2000 NBA MVP | 17 |
| 1999-2001 Broadway musical revue | 32 |
| 1999-2004 Olds | 14 |
| 1999-2004 Oldsmobile | 20 |
| 1999-2004 Oldsmobile model | 26 |
| 1999-2006 NBC series | 20 |
| 1999-2007 House speaker Dennis | 30 |
| 19th Amendment backer | 21 |
| 19th Amendment beneficiaries | 28 |
| 19th Amendment beneficiary | 26 |
| 19th Amendment champion | 23 |
| 19th Amendment proponent | 24 |
| 19th Amendment subject | 22 |
| 19th book of the Bible | 22 |
| 19th c. actor Booth | 19 |
| 19th C. American painter | 24 |
| 19th C. art style emphasizing nature | 36 |
| 19th C. engine engineer | 23 |
| 19th c. French landscapist | 26 |
| 19th C. French writer | 21 |
| 19th C. German physicist | 24 |
| 19th C. humorist Bill | 21 |
| 19th C. movement | 16 |
| 19th C. painter | 15 |
| 19th C. poet | 12 |
| 19th century canal name | 23 |
| 19th century cartoonist | 23 |
| 19th century Chief Justice Roger ___ | 36 |
| 19th century communications pioneer | 35 |
| 19th century Dublin mayor known as "The Liberator" | 60 |
| 19th century England | 20 |
| 19th Century folk song | 22 |
| 19th century French composer | 28 |
| 19th century inventor Howe | 26 |
| 19th century political cartoonist Thomas | 40 |
| 19th Century socialite Peggy | 28 |
| 19th century soprano __ Patti | 29 |
| 19th century South Seas novel | 29 |
| 19th century tale of South Seas travel | 38 |
| 19th century writer of inspiring novels | 39 |
| 19th dynasty Egyptian king | 26 |
| 19th dynasty's founder | 26 |
| 19th Greek letter | 17 |
| 19th Hebrew letter | 18 |
| 19th hole | 9 |
| 19th in a Greek series | 22 |
| 19th in a series | 16 |
| 19th letter | 11 |
| 19th letter of Greek alphabet: pl. | 34 |
| 19th letter of Hebrew alphabet | 30 |
| 19th letter of the Greek alphabet | 33 |
| 19th letters | 12 |
| 19th of 24 | 10 |
| 19th of 24 Greek letters | 24 |
| 19th of 26 | 10 |
| 19th pres.'s monogram | 25 |
| 19th president | 14 |
| 19th U.S. president | 19 |
| 19th ___ (golf clubhouse) | 25 |
| 19th-/20th-century U.S. portraitist | 35 |
| 19th-c. French landscapist | 26 |
| 19th-cen. alliance | 18 |
| 19th-century "Divina Commedia" translator Henry Francis ___ | 69 |
| 19th-century abbot and scientist | 32 |
| 19th-century abolitionist | 25 |
| 19th-century actor ___ Booth | 28 |