| Year | Katherine Wright Award (established 1981, inactive from 1983-1989) | Award of Achievement (established 1997) | Award of Merit (established 1990) | George Palmer Putnam Award (established 2006) | Award of Inspiration (established 1995) | President's Award (established 1996) |
| 2026 | TBA | TBA | TBA | TBA | TBA | TBA |
| 2025 | Kim Dell | Beth White Lori Plourd Peggy Doyle | Richard Blevins | Sunita Williams | Lori Plourd | |
| 2024 | Theresa Claiborne | Laurene (Fielder) McEneny Dr. Barbara Gruber Kelli O'Donnell | Catherine Press | Edward "The Legend" Marquet | Sisters of the Skies | The 99s Professional Pilot Leadership Initiative (PPLI) |
| 2023 | Julie Clark | Joy Parker Blackwood Mary Build Jo-Ann Prater | Francois Leh | Nicole Malachowski | Jan McKenzie | |
| 2022 | Jill R. Meyers | Ursula Davidson Jean "Sunny" Schiffmann | Jim Riviere | Zara Rutherford | Ellen Nobles-Harris | |
| 2021 | Major Eleanor Morgan | Dr. Rebecca K. Lutte Myra Bugbee Stephanie Wells | Indian Women Pilots' Association (IWPA) | Harry Pride | Ivana Alvares-Marshall | Deb Henneberry |
| 2020 | Dorothy Cochrane | Dr. Jacque Boyd Marion Jayne (posthumously) | Captain Barry Schiff | Ron Machado | The Mercury 13 | Laura Ohrenberg |
| 2019 | Barbara Walters-Phillips | Madeleine Monaco Kelli Kuntz Gretchen Jahn | David Oreck | Thelma Cull | Cecile Hatfield | |
| 2018 | Anne Bridge Baddour | Col. Kathryn Hughes, MD Elaine Morrow | Tammy Duckworth | Linda Horn | ||
| 2017 | Major Chrystina Jones | Katherine Macario Diana Stanger Sabina Shrestha | Sean Tucker | Art Phillips | Bee Haydu | Roberta Roe |
| 2016 | Priscilla (Pat) Blum | Jody McCarrell Rita Eaves Wilma Melville | Harry Weatherford | Woody Lesikar | Kathy Fox | Cecile Hatfield |
| 2015 | Patricia Pearce | Joan Kerwin Dr. Petra Illig Heather Strezick | Jerry Hunter | Alia Twal | Pat McCollum | |
| 2014 | Judith Neuffer Bruner | Nadine Sugden Joan Mace Carol Sokatch | Joseph Gordon Sanders | Bob Delong, David Pierce | Terry Carbonell | Mary Wunder |
| 2013 | Kim De Groh, Mary S. Feik | Carole Sutton Deborah V. Gallaway | David Black | Bob Jones | Catherine "Kitty" Houghton | Clay Lacy |
| 2012 | Captain Laura B. Easton, USAF | Anneli Kokkola Deborah Rihn-Harvey Jean Murry and Delia Greer | Erich Kustatscher | Dean Jaros | Mireille Goyder | Pat Prentiss |
| 2011 | Frances S. "Fran" Bera | Lisa Cotham Mary Margaret Wunder Emaily Howell Warner Danielle Aitchison | Jerry Clubb | Gail Mesa Norman | Terri Donner | The Ninety-Nines Headquarters Staff |
| 2010 | Master Sargeant Kimberly L. Muhlecke, USAF | Mimi Tompkins Fran Bera Fran Strubeck Dr. Anne Spoerry | Lt. Phillip Daalton | John "Ray" Copeland | Carolyn Grangaard Smith | Susan Loricchio |
| 2009 | Donna Shirley | Ellen Nobles-Harris Susan Liebeler | Rita Creighton | Hampton Hotels | Eileen Collins | Virginia Harmer |
| 2008 | Captain Karen Lee | Pearl Bragg Laska Chamberlain Verna Steele West | Northwoods AirLifeLine | Glen Morrow | Vee Gordon | Larry Stubblefield and LWPB Architecture |
| 2007 | Colonel Catherine A. Chilton | Aero Club of New England | Women in Aviation, International | Sue Phillips | ||
| 2006 | Annie Castor Glenn | Dianne Lauren Cole | Richard MacDonald | Robert Feigenbaum, Edward Sharp | Sondra Ridgeway | Publications Committee |
| 2005 | Patty Wagstaff | Gene Nora Jessen | Pamela Ann Collings | Jenny Beatty | ||
| 2004 | Gertrude Rogallo | Ardyth Williams | Belinda Bender | Barbara Sierchio and Nancy Wright | Rita Adams | |
| 2003 | Eilene M. Galloway | Lois Feigenbaum | Louise Foudray | Char Falkenberg | Pamela O'Brien | |
| 2002 | Evelyn Bryan Johnson | Marion "Babe" Ruth | AOPA | Vicky Anderson, Susan Theurkauf | ||
| 2001 | Fay Gillis Wells | Yvonne Pateman | C. Gilbert Taylor | Celia Vanderpool | ||
| 2000 | Carroll W. Suggs | Anita L. Lewis | Orville Wilber Tosch | Elaine Morrow | ||
| 1999 | Athley Gamber | Maybelle Fletcher | Cindy Rusher | Oklahoma Chapter | Katherine Macario | |
| 1998 | Ramona Ann Ardaiz | Ida Van Smith Dunn | Marilyn Copeland | Ana Camberos Province | ||
| 1997 | Doris Lockness | Louise Thadden | Faye Gillis Wells | |||
| 1996 | Virginia M. "Ginny" Schweizer | Pauline Glasson | Aschna Donnels | Gene Nora Jessen, Claire Walters | ||
| 1995 | Audrey Poberezny | Charter Members of The 99s | ||||
| 1994 | Nadine Jeppesen | Evelyn Bryan Johnson, William Kershner | ||||
| 1993 | June De Etta Maule | Commander Rosemary Bryant Conatser Mariner, Lorna DeBlicquy, H. Glenn Buffington, WASPs | ||||
| 1992 | Elizabeth "Betty" Pfister | Litfia El-Nadia, Thon Giffith, Bobbi Trout | ||||
| 1991 | Olive Ann Beech | Alice Hammond, Nancy Bird Walton, Olive Ann Beech, John Baker, Hazel Jones | ||||
| 1990 | Ascha B. Peacock Donnels | Pat and Sheldon Roberts, Muriel Earhart Morrissey, Jeana Yeager, Mimi Tompkins, Gaby Kennard | ||||
| 1982 | Anne Morrow Lindbergh | |||||
| 1981 | Moya Lear |
1992 -- NAA/EAA/99s Award: Grace Harris
2001 -- Governors Achievement Award: Marilyn Copeland
2012 -- Special Recognition: Museum of Women Pilots Founders: Vicky Anderson, Thon Griffith, Virginia Harmer, Lu Hollander, Gene Nora Jessen, Bev LaBrie, Anita Lewis, Vic Lewis, C.J. Stawn, Susan Theurkauf, Claire Walters, Verna West
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Cathleen (Cathy) SteeleI have been an active CFI since 1998 and have accrued over 6000 of dual given. Previously I have been the Chief Flight Instructor at a Part 141 flight training school located at KBWI and also served as the Chief Flight Instructor at the first flight training academy in Nepal. Currently I am an independent Cirrus Instructor pilot with Platinum status.
Instructor Ratings: CFI, CFII
Location: Baltimore, MD, United States 
Contact InstructorTo: Cathleen Steele
Location: Baltimore, MD, United States