| Date | Grid | Clue | Author |
| Saturday, October 13, 2012 | 36A | Skater with many trophies | Barry C. Silk |
| Tuesday, October 9, 2012 | 31D | Hockey defender Bobby | John Guzzetta |
| Tuesday, July 3, 2012 | 23A | Hockey player Bobby | Robyn Weintraub |
| Wednesday, March 14, 2012 | 41A | Bobby of the rink | Dave Sarpola |
| Wednesday, February 15, 2012 | 55A | Bruins legend (2) | Peter A. Collins |
| Wednesday, December 28, 2011 | 9D | Notable #4 on the ice | Louis Zulli |
| Thursday, December 15, 2011 | 15A | Recipient of three consecutive Hart Trophies | Jim Hilger |
| Wednesday, October 19, 2011 | 60D | Boston Garden legend Bobby | Patrick Berry |
| Thursday, September 29, 2011 | 2D | Bomber pilot in "Catch-22" (2) | Ben Fish |
| Sunday, July 3, 2011 | 127A | "Catch-22" bomber pilot (3) | Pete Muller |
| Thursday, May 19, 2011 | 14A | Two-time Art Ross Trophy winner (2) | Paula Gamache |
| Sunday, May 1, 2011 | 15D | Bobby on the ice (2) | Xan Vongsathorn |
| Sunday, February 6, 2011 | 28A | Fast-skating #4 | David J. Kahn |
| Monday, January 17, 2011 | 22D | Canadian-born hockey great (3) | Elizabeth C. Gorski |
| Thursday, October 28, 2010 | 31D | Bomber pilot in "Catch-22" (2) | David J. Kahn |
| Friday, June 25, 2010 | 36A | Yossarian's tentmate in "Catch-22" (4) | Robin Schulman and Byron Walden |
| Sunday, May 16, 2010 | 17D | Only defenseman to have won the N.H.L. scoring title | Matt Ginsberg |
| Wednesday, April 28, 2010 | 23D | Norris Trophy winner for eight consecutive years | Andrea Carla Michaels and Peter L. Stein |
| Sunday, April 25, 2010 | 5D | Canadian-born hockey great (3) | Elizabeth C. Gorski |
| Sunday, January 31, 2010 | 74A | "Catch-22" bomber pilot (3) | Tony Orbach and Andrea Carla Michaels |
| Thursday, January 7, 2010 | 34D | CBS newsman Bob | Xan Vongsathorn |
| Sunday, December 20, 2009 | 53A | Bruin great | Alan Arbesfeld |
| Sunday, October 18, 2009 | 81A | Canadian-born hockey great (3) | Elizabeth C. Gorski |
| Monday, October 12, 2009 | 63D | Bobby who was #4 at Boston Garden | Richard Chisholm |
| Monday, September 7, 2009 | 66D | Hockey's Bobby (7) | Andrea Carla Michaels and Ashish Vengsarkar |
| Sunday, July 19, 2009 | 38A | "Catch-22" bomber pilot (3) | Lynn Lempel |
| Wednesday, April 1, 2009 | 6D | Bruins' retired "4" | Ed Stein and Paula Gamache |
| Sunday, March 29, 2009 | 18D | Peace Nobelist John Boyd ___ (2) | Elizabeth C. Gorski |
| Sunday, December 28, 2008 | 14D | Yossarian's tentmate in "Catch-22" (4) | Patrick Berry |
| Friday, November 28, 2008 | 11D | His #4 was retired (2) | Joe Krozel |
| Friday, September 12, 2008 | 38A | Lord John Boyd ___, winner of the 1949 Nobel Peace Prize | Natan Last |
| Sunday, August 10, 2008 | 75A | Yossarian's tentmate, in "Catch-22" (4) | Will Nediger |
| Thursday, July 31, 2008 | 2D | 1967 N.H.L. rookie of the year (2) | Allan E. Parrish |
| Sunday, April 20, 2008 | 30A | Eight-time Norris Trophy winner (10) | John Farmer |
| Thursday, April 10, 2008 | 32D | Three-time Hart Trophy winner (6) | David J. Kahn |
| Sunday, January 27, 2008 | 13D | Sports legend whose #4 was retired | Mike Nothnagel |
| Monday, January 14, 2008 | 35A | Bobby of the N.H.L. (2) | Robert Dillman |
| Wednesday, January 9, 2008 | 50D | Hockey's Bobby (7) | John Farmer |
| Tuesday, November 6, 2007 | 7D | Bobby of the Bruins (4) | John Underwood |
| Wednesday, October 24, 2007 | 11D | Bobby of Boston | Patrick Blindauer |
| Monday, July 23, 2007 | 27D | Bobby ___, the only N.H.L.'er to win the Hart, Norris, Ross and Smythe trophies in the same year | Randall J. Hartman |
| Wednesday, April 11, 2007 | 7D | Boston rink legend (2) | Bruce Adams |
| Tuesday, February 13, 2007 | 51D | 1960's-70's Boston Garden hero | Nancy Salomon and Harvey Estes |
| Monday, February 12, 2007 | 4D | Hockey legend Bobby (2) | Lynn Lempel |
| Wednesday, February 7, 2007 | 60D | Bruins legend (2) | David Kwong |
| Tuesday, December 26, 2006 | 38A | The Bruins' #4 | C. W. Stewart |
| Tuesday, October 17, 2006 | 65D | Bruin legend | Alan Arbesfeld |
| Sunday, September 10, 2006 | 89A | New England hockey hero | Joe DiPietro |
| Wednesday, August 9, 2006 | 35D | Boston rink legend (2) | Maxwell H. D. Johnson Jr. |
| Friday, July 21, 2006 | 16A | #4 for Boston | Kyle Mahowald |
| Wednesday, May 31, 2006 | 58A | Bobby of the Bruins (4) | Trip Payne |
| Wednesday, April 12, 2006 | 37D | Legendary Bruin | Elizabeth C. Gorski |
| Saturday, April 1, 2006 | 15A | #4, once, in Boston | Kevan Choset and David Kwong |
| Sunday, January 15, 2006 | 62A | Notable #4 with a stick | Richard Silvestri |
| Tuesday, November 29, 2005 | 34D | Bruins great Bobby | Adam Cohen |
| Sunday, November 20, 2005 | 89A | Eight-time Norris Trophy winner (10) | Patrick Merrell |
| Friday, November 4, 2005 | 24A | Scottish Peace Nobelist John Boyd ___ | Martin Ashwood-Smith |
| Thursday, October 6, 2005 | 58D | Legendary stick figure | Daniel C. Bryant |
| Sunday, September 11, 2005 | 79A | Yossarian's tentmate, in "Catch-22" (4) | Patrick Berry |
| Friday, March 18, 2005 | 15A | He racked up 645 assists | Ed Early |
| Sunday, January 16, 2005 | 2D | Legend on the ice (2) | Damon J. Gulczynski |
| Tuesday, November 2, 2004 | 58A | Bobby of hockey (3) | Patrick Merrell |
| Wednesday, October 20, 2004 | 58A | Bruin who wore a 4 | Elizabeth C. Gorski |
| Sunday, September 26, 2004 | 62D | Boston retired his number 4 | Joe DiPietro |
| Saturday, May 22, 2004 | 9D | Skating legend | Mark Diehl |
| Sunday, May 9, 2004 | 91D | Goal-oriented guy | Charles M. Deber |
| Saturday, April 10, 2004 | 52D | Famous Bruin #4 | Mark Diehl |
| Friday, November 28, 2003 | 19A | Plane crasher in "Catch-22" | Brendan Emmett Quigley |
| Monday, September 15, 2003 | 35A | Bruin legend Bobby (2) | Sheldon Benardo |
| Sunday, August 3, 2003 | 74D | Two-time Art Ross Trophy winner (2) | Jim Page |
| Monday, March 17, 2003 | 32D | Bobby of the Bruins (4) | David Ainslie Macleod |
| Friday, March 14, 2003 | 35A | He chalked up 915 points | Kevin Hagen |
| Wednesday, February 19, 2003 | 41A | Bobby on the ice (2) | Sarah Keller |
| Monday, February 17, 2003 | 40A | Bruin Bobby (2) | Alan Arbesfeld |
| Monday, February 3, 2003 | 35A | Bruin legend Bobby (2) | Sheldon Benardo |
| Sunday, December 15, 2002 | 2D | Hockey's 1967 Calder Trophy winner | RIchard Hughes |
| Monday, December 9, 2002 | 59A | Hockey great Bobby | Sarah Keller |
| Monday, October 7, 2002 | 60A | Bobby of the N.H.L. (2) | Greg Staples |
| Thursday, May 9, 2002 | 49A | 1970 Sportsman of the Year | Cathy Millhauser |
| Sunday, May 5, 2002 | 74A | Mary ___, on whose story "All About Eve" is based | Patrick Berry |
| Sunday, February 3, 2002 | 50A | N.H.L. M.V.P., 1970-72 | Richard Silvestri |
| Thursday, December 27, 2001 | 19D | Famous Bruin (2) | Patrick Berry |
| Sunday, December 23, 2001 | 50D | Hall-of-Famer Bobby | Frances Hansen |
| Wednesday, December 12, 2001 | 55A | Hall-of-Famer nicknamed "Bobby Hockey" | Peter Gordon |
| Saturday, December 8, 2001 | 31D | 1949 Peace Prize winner Lord John Boyd ___ | Rich Norris |
| Wednesday, October 24, 2001 | 33D | Eight-time Norris Trophy winner (10) | Sarah Keller |
| Sunday, August 5, 2001 | 116D | 1967 Rookie of the Year | Peter Gordon |
| Saturday, July 21, 2001 | 59D | Ice legend | Mark Diehl |
| Tuesday, November 21, 2000 | 32D | Boston Bruins legend | Robert Zimmerman |
| Saturday, November 4, 2000 | 50A | Three-time Hart Trophy winner (6) | Rich Norris |
| Sunday, October 15, 2000 | 54D | Athlete who wrote "My Game" | Patrick Berry |
| Sunday, October 1, 2000 | 89D | John Boyd ___, 1949 Peace Nobelist | Nancy Nicholson Joline |
| Sunday, September 24, 2000 | 66D | #4 on ice | Randolph Ross |
| Sunday, August 27, 2000 | 22A | Legend on the ice (2) | Dana Motley |
| Monday, July 10, 2000 | 61D | Hockey's Bobby (7) | Gene Newman |
| Saturday, June 24, 2000 | 54A | "Catch-22" pilot (2) | Nancy Joline |
| Saturday, May 27, 2000 | 6D | Legendary iceman | Robert H. Wolfe |
| Sunday, April 2, 2000 | 111A | 1967 N.H.L. Rookie of the Year (2) | Nancy Salomon and Harvey Estes |
| Friday, March 31, 2000 | 38A | Bruin Hall-of-Fame defenseman | Nancy Salomon and Harvey Estes |
| Sunday, February 20, 2000 | 54D | Eight-time Norris Trophy winner (10) | Trip Payne |
| Sunday, November 14, 1999 | 4D | His #4 was retired (2) | Lloyd E. Pollet |
| Monday, November 8, 1999 | 6D | Bobby of hockey (3) | Kent Lorentzen |
| Saturday, November 6, 1999 | 29A | "Catch-22" pilot (2) | Joan Bayer Williamson |
| Sunday, September 26, 1999 | 46A | Two-time Smythe Trophy winner (2) | Randolph Ross |
| Wednesday, July 21, 1999 | 61D | Eight-time Norris Trophy winner (10) | Noah Dephoure |
| Wednesday, May 19, 1999 | 57A | Bruin whose #4 jersey is now retired | Elizabeth C. Gorski |
| Thursday, April 22, 1999 | 32D | Onetime Bruin star | David J. Kahn |
| Wednesday, April 21, 1999 | 30A | Bobby of hockey (3) | Mary E. Brindamour |
| Wednesday, April 7, 1999 | 13D | N.H.L. Hall-of-Famer since 1979 (2) | Rich Norris |
| Sunday, February 21, 1999 | 27A | Winner of eight Norris Trophies | Fred Piscop |
| Thursday, December 17, 1998 | 30D | Onetime Esposito teammate | David J. Kahn |
| Monday, August 24, 1998 | 35A | Hockey legend Bobby (2) | Alan Jay Weiss |
| Wednesday, August 19, 1998 | 41D | Hockey's Bobby (7) | Alfio Micci |
| Saturday, July 25, 1998 | 6D | 1970 Stanley Cup hero | Robert H. Wolfe |
| Tuesday, July 14, 1998 | 4D | Hart Trophy winner, 1970-72 (2) | Raymond Hamel |
| Friday, March 27, 1998 | 25D | Peace Nobelist John Boyd ___ (2) | Alan Jay Weiss |
| Saturday, March 21, 1998 | 4D | N.H.L. Hall-of-Famer since 1979 (2) | Rich Norris |
| Monday, February 9, 1998 | 5D | Bobby of the Bruins (4) | Robert Dillman |
| Sunday, November 30, 1997 | 88A | Boston's Bobby | Charles Deber |
| Monday, October 13, 1997 | 50A | Hockey's Bobby (7) | Gregory E. Paul |
| Saturday, October 11, 1997 | 10D | Three-time Hart Trophy winner (6) | Fred Piscop |
| Thursday, June 26, 1997 | 6D | Famous Bruin (2) | Martin Ashwood-Smith |
| Saturday, January 11, 1997 | 49A | Hart Trophy winner, 1970-72 (2) | R. Norris |
| Saturday, October 12, 1996 | 18A | Eight-time Norris Trophy winner (10) | R. Norris |
| Tuesday, October 8, 1996 | 36D | Puckster Bobby | E. C. Gorski |
| Sunday, June 16, 1996 | 89D | Eight-time Norris Trophy winner (10) | N. N. Joline |
| Thursday, June 6, 1996 | 54D | Bruin of yore | A. J. Santora |
| Thursday, May 16, 1996 | 38D | 1949 Peace Nobelist John Boyd___ | F. Longo |
| Wednesday, May 1, 1996 | 8D | Rink great | F. Piscop |
| Friday, April 19, 1996 | 35D | Eight-time Norris Trophy winner (10) | A. Micci |
| Friday, November 10, 1995 | 31D | Ice hockey legend | Bryant White |
| Monday, November 6, 1995 | 20A | Iceman Bobby | Roger H. Courtney |
| Thursday, October 5, 1995 | 9D | Three-time Hart Trophy winner (6) | Christopher Page |
| Tuesday, September 5, 1995 | 32A | #4 of the Bruins | Jonathan Schmatzbach |
| Friday, July 28, 1995 | 36D | Former N.H.L. great | Rich Norris |
| Sunday, April 16, 1995 | 94D | Hockey Hall-of-Famer | Matt Gaffney |
| Sunday, March 12, 1995 | 99A | Eight-time Norris Trophy winner (10) | Charles M. Deber |
| Monday, January 30, 1995 | 9D | Hockey's Bobby (7) | Ernie Furtado |
| Monday, January 23, 1995 | 6D | Bruin Bobby (2) | Sidney L. Robbins |
| Thursday, January 19, 1995 | 8D | Celebrated Bruin blueliner | Bryant White |
| Thursday, December 29, 1994 | 45D | Three-time Hart Trophy winner (6) | Jim Page |
| Sunday, September 18, 1994 | 33D | Three-time Hart Trophy winner (6) | Merl Reagle |
| Thursday, August 11, 1994 | 5D | Two-time Smythe Trophy winner (2) | Bryant White |
| Monday, July 18, 1994 | 54D | Hockey's Bobby (7) | Wayne Robert Williams |
| Sunday, June 19, 1994 | 5D | Bruins great | Nancy Scandrett Ross |
| Thursday, February 17, 1994 | 7D | Eight-time Norris Trophy winner (10) | Brett Blaylock |
| Sunday, January 16, 1994 | 37D | Boston sports legend | Ernst Theimer |
| Sunday, November 21, 1993 | 66A | 1968-75 Norris Trophy winner | Peter Gordon |