| Date | Size | Title | Author |
| January 3, 1999 | 21 x 21 | NY Times, Sun, Jan 03, 1999 "Proverbial Conflicts" | Randolph Ross |
| January 10, 1999 | 21 x 21 | NY Times, Sun, Jan 10, 1999 "Actually Spoken By 121-Across" | David J. Kahn |
| January 17, 1999 | 21 x 21 | NY Times, Sun, Jan 17, 1999 "Following Orders" | Cathy Millhauser |
| January 24, 1999 | 21 x 21 | NY Times, Sun, Jan 24, 1999 "Cross Word Puzzle" | Robert Malinow |
| January 31, 1999 | 21 x 21 | NY Times, Sun, Jan 31, 1999 "Gaining Weight" | Manny Nosowsky |
| February 7, 1999 | 21 x 21 | NY Times, Sun, Feb 07, 1999 "Hidden Zoo" | Nancy Nicholson Joline |
| February 14, 1999 | 21 x 21 | NY Times, Sun, Feb 14, 1999 "Leading Singers" | Elizabeth Gorski |
| February 21, 1999 | 21 x 21 | NY Times, Sun, Feb 21, 1999 "Off" Broadway | Fred Piscop |
| February 28, 1999 | 21 x 21 | NY Times, Sun, Feb 28, 1999 "Alien Abductions" | Dave Tuller |
| March 7, 1999 | 21 x 21 | NY Times, Sun, Mar 07, 1999 "Golly Gee" | Randolph Ross |
| March 14, 1999 | 21 x 21 | NY Times, Sun, Mar 14, 1999 "In Other Words" | Martin Schneider |
| March 21, 1999 | 21 x 21 | NY Times, Sun, Mar 21, 1999 "St. Elsewhere" | Lloyd E. Pollet |
| March 28, 1999 | 21 x 21 | NY Times, Sunday, March 28, 1999 Railroad Crossings | Cathy Allis Millhauser |
| April 4, 1999 | 21 x 21 | NY Times, Sun, Apr 04, 1999 "That Woman" | Richard Silvestri |
| April 11, 1999 | 21 x 21 | NY Times, Sun, Apr 11, 1999 "Spring Dream" | Matt Gaffney |
| April 18, 1999 | 25 x 25 | NY Times, Sun, Apr 18, 1999 "Rhymes of the Centuries" (Hard Clues) | Frank Longo |
| April 25, 1999 | 21 x 21 | NY Times, Sun, Apr 25, 1999 "Sez Who?" | Joe DiPietro |
| May 2, 1999 | 21 x 21 | NY Times, Sun, May 02, 1999 "It's Got Sizzle!" | Jim Page |
| May 9, 1999 | 21 x 21 | NY Times, Sun, May 09, 1999 LIKELY TO BE HEARD BY MOTHER... | Nancy Nicholson Joline |
| May 16, 1999 | 25 x 25 | NY Times, Sun, May 16, 1999 FAMOUS FEMALES IN FILM (Hard Clues) | Nancy Nicholson Joline |
| May 23, 1999 | 21 x 21 | NY Times, Sun, May 23, 1999 CO2 | Harvey Estes and Nancy Salomon |
| May 30, 1999 | 21 x 21 | NY Times, Sun, May 30, 1999 APOSTROPHES IN THE HEADLINES | Cathy Millhauser |
| June 6, 1999 | 25 x 25 | NY Times, Sun, Jun 06, 1999 CHOICE WORDS (Hard Clues) | David J. Kahn |
| June 13, 1999 | 21 x 21 | NY Times, Sun, Jun 13, 1999 LE PUZZLE | Rich Norris |
| June 20, 1999 | 21 x 21 | NY Times, Sunday, June 20, 1999 Tea For Two | Manny Nosowsky |
| June 27, 1999 | 21 x 21 | NY Times, Sun, Jun 27, 1999 PERSONAL SCORE | Robert Malinow |
| July 4, 1999 | 21 x 21 | NY Times, Sun, Jul 04, 1999 FOURLOCKS | Greg Staples |
| July 11, 1999 | 21 x 21 | NY Times, Sun, Jul 11, 1999 MISLEADING MENAGERIE | Nancy Salomon |
| July 18, 1999 | 21 x 21 | NY Times, Sunday, July 18, 1999 Just For Openers | Nancy Nicholson Joline |
| July 25, 1999 | 21 x 21 | NY Times, Sun, Jul 25, 1999 MIRROR MIRROR | Charles M. Deber |
| August 1, 1999 | 21 x 21 | NY Times, Sun, Aug 01, 1999 AWAY WITH WORDS | Randolph Ross |
| August 8, 1999 | 21 x 21 | NY Times, Sun, Aug 08, 1999 BOYS WILL BE GIRLS | Brendan Emmett Quigley |
| August 15, 1999 | 21 x 21 | NY Times, Sun, Aug 15, 1999 NETWORKING | David J. Kahn |
| August 22, 1999 | 21 x 21 | NY Times, Sun, Aug 22, 1999 EXCHANGES | Raymond Hamel |
| August 29, 1999 | 21 x 21 | NY Times, Sun, Aug 29, 1999 TRADEMARKS | Lou and Fran Sabin |
| September 5, 1999 | 21 x 21 | NY Times, Sun, Sep 05, 1999 STARTING OVER? | Elizabeth C. Gorski |
| September 12, 1999 | 21 x 21 | NY Times, Sun, Sep 12, 1999 RARE BIRDS | Nancy Scandrett Ross |
| September 19, 1999 | 25 x 25 | NY Times, Sun, Sep 19, 1999 ANAGRAMMED INVENTIONS (Hard Clues) | Manny Nosowsky |
| September 26, 1999 | 23 x 23 | NY Times, Sun, Sep 26, 1999 "SUB" TITLES | Randolph Ross |
| October 3, 1999 | 21 x 21 | NY Times, Sun, Oct 03, 1999 NO HOLDS BARD | Fred Piscop |
| October 10, 1999 | 21 x 21 | NY Times, Sun, Oct 10, 1999 MY KINDA PUZZLE | Cathy Millhauser |
| October 17, 1999 | 25 x 25 | NY Times, Sun, Oct 17, 1999 JUST TRY ME! (Hard Clues) | Bob and Sharon Klahn |
| October 24, 1999 | 21 x 21 | NY Times, Sun, Oct 24, 1999 MALE BONDING | Nancy Salomon |
| October 31, 1999 | 23 x 23 | NY Times, Sunday, October 31, 1999 Twin States | Frank A. Longo |
| November 7, 1999 | 21 x 21 | NY Times, Sun, Nov 07, 1999 CUES | Brendan Emmett Quigley |
| November 14, 1999 | 21 x 21 | NY Times, Sun, Nov 14, 1999 STARS "R" US | Lloyd E. Pollet |
| November 21, 1999 | 21 x 21 | NY Times, Sun, Nov 21, 1999 ODD COUPLES | Patrick D. Berry |
| November 28, 1999 | 21 x 21 | NY Times, Sun, Nov 28, 1999 PLURAL PERPLEXITY | Cathy Millhauser |
| December 5, 1999 | 25 x 25 | NY Times, Sun, Dec 05, 1999 PREDICTIONS FOR THE NEXT MILLENNIUM (Hard Clues) | Joe DiPietro |
| December 12, 1999 | 21 x 21 | NY Times, Sun, Dec 12, 1999 TURIN THE COUNTRY | Richard Silvestri |
| December 19, 1999 | 21 x 21 | NY Times, Sun, Dec 19, 1999 CHRISTMAS CACHE | Frances Hansen |
| December 26, 1999 | 21 x 21 | NY Times, Sun, Dec 26, 1999 WORDS HILLBILLY-STYLE | Greg Staples |