| 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 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 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 |