| Date | Size | Title | Author |
| January 3, 1999 | 21 x 21 | Proverbial Conflicts | Randolph Ross |
| January 10, 1999 | 21 x 21 | Actually Spoken By 121-Across | David J. Kahn |
| January 17, 1999 | 21 x 21 | Following Orders | Cathy Millhauser |
| January 24, 1999 | 21 x 21 | Cross Word Puzzle | Robert Malinow |
| January 31, 1999 | 21 x 21 | Gaining Weight | Manny Nosowsky |
| February 7, 1999 | 21 x 21 | Hidden Zoo | Nancy Nicholson Joline |
| February 14, 1999 | 21 x 21 | Leading Singers | Elizabeth Gorski |
| February 21, 1999 | 21 x 21 | Off Broadway | Fred Piscop |
| February 28, 1999 | 21 x 21 | Alien Abductions | Dave Tuller |
| March 7, 1999 | 21 x 21 | Golly Gee | Randolph Ross |
| March 14, 1999 | 21 x 21 | In Other Words | Martin Schneider |
| March 21, 1999 | 21 x 21 | St. Elsewhere | Lloyd E. Pollet |
| March 28, 1999 | 21 x 21 | Railroad Crossings | Cathy Allis Millhauser |
| April 4, 1999 | 21 x 21 | That Woman | Richard Silvestri |
| April 11, 1999 | 21 x 21 | Spring Dream | Matt Gaffney |
| April 18, 1999 | 25 x 25 | Rhymes of the Centuries (hard clues) | Frank Longo |
| April 25, 1999 | 21 x 21 | Sez Who? | Joe DiPietro |
| May 2, 1999 | 21 x 21 | It's Got Sizzle! | Jim Page |
| May 9, 1999 | 21 x 21 | Likely to be Heard by Mother... | Nancy Nicholson Joline |
| May 16, 1999 | 25 x 25 | Famous Females in Film (hard clues) | Nancy Nicholson Joline |
| May 23, 1999 | 21 x 21 | Co2 | Harvey Estes and Nancy Salomon |
| May 30, 1999 | 21 x 21 | Apostrophes in the Headlines | Cathy Millhauser |
| June 6, 1999 | 25 x 25 | Choice Words (hard clues) | David J. Kahn |
| June 13, 1999 | 21 x 21 | Le Puzzle | Rich Norris |
| June 20, 1999 | 21 x 21 | Tea For Two | Manny Nosowsky |
| June 27, 1999 | 21 x 21 | Personal Score | Robert Malinow |
| July 4, 1999 | 21 x 21 | Fourlocks | Greg Staples |
| July 11, 1999 | 21 x 21 | Misleading Menagerie | Nancy Salomon |
| July 18, 1999 | 21 x 21 | Just For Openers | Nancy Nicholson Joline |
| July 25, 1999 | 21 x 21 | Mirror Mirror | Charles M. Deber |
| August 1, 1999 | 21 x 21 | Away with Words | Randolph Ross |
| August 8, 1999 | 21 x 21 | Boys Will be Girls | Brendan Emmett Quigley |
| August 15, 1999 | 21 x 21 | Networking | David J. Kahn |
| August 22, 1999 | 21 x 21 | Exchanges | Raymond Hamel |
| August 29, 1999 | 21 x 21 | Trademarks | Lou and Fran Sabin |
| September 5, 1999 | 21 x 21 | Starting Over? | Elizabeth C. Gorski |
| September 12, 1999 | 21 x 21 | Rare Birds | Nancy Scandrett Ross |
| September 19, 1999 | 25 x 25 | Anagrammed Inventions (hard clues) | Manny Nosowsky |
| September 26, 1999 | 23 x 23 | "Sub" Titles | Randolph Ross |
| October 3, 1999 | 21 x 21 | No Holds Bard | Fred Piscop |
| October 10, 1999 | 21 x 21 | My Kinda Puzzle | Cathy Millhauser |
| October 17, 1999 | 25 x 25 | Just Try Me! (hard clues) | Bob and Sharon Klahn |
| October 24, 1999 | 21 x 21 | Male Bonding | Nancy Salomon |
| October 31, 1999 | 23 x 23 | Twin States | Frank A. Longo |
| November 7, 1999 | 21 x 21 | Cues | Brendan Emmett Quigley |
| November 14, 1999 | 21 x 21 | Stars "R" Us | Lloyd E. Pollet |
| November 21, 1999 | 21 x 21 | Odd Couples | Patrick D. Berry |
| November 28, 1999 | 21 x 21 | Plural Perplexity | Cathy Millhauser |
| December 5, 1999 | 25 x 25 | Predictions for the Next Millennium (hard clues) | Joe DiPietro |
| December 12, 1999 | 21 x 21 | Turin the Country | Richard Silvestri |
| December 19, 1999 | 21 x 21 | Christmas Cache | Frances Hansen |
| December 26, 1999 | 21 x 21 | Words Hillbilly-Style | Greg Staples |