| 2026-05-15 | Miss Doolittle of "Pygmalion" |
| 2024-09-14 | Musical character who sings "Just You Wait" |
| 2024-01-30 | Doolittle of "My Fair Lady" |
| 2023-02-07 | Sister to Angelica and Peggy in "Hamilton" |
| 2021-05-25 | Doolittle of "Pygmalion" |
| 2020-11-29 | One of the Schuyler sisters in "Hamilton" |
| 2020-06-21 | "My Fair Lady" protagonist |
| 2018-12-05 | Slave in "Uncle Tom's Cabin" |
| 2017-08-18 | Spouse of Alexander Hamilton |
| 2017-02-01 | Lady of "My Fair Lady" |
| 2017-01-31 | Woman who sings "Burn" in "Hamilton" |
| 2016-12-15 | Mrs. Alexander Hamilton |
| 2016-06-30 | "My Fair Lady" lady |
| 2015-11-26 | Musical character who sings "Wouldn't it be loverly?" |
| 2015-08-18 | Slave woman in "Uncle Tom's Cabin" |
| 2015-08-10 | "My Fair Lady" lady |
| 2015-07-20 | Doolittle of fiction |
| 2014-07-25 | The "you" in "On the Street Where You Live" |
| 2013-11-13 | Pupil of 'enry 'iggins |
| 2013-09-11 | 'Enry's fair lady |
| 2012-12-25 | Doolittle played by Audrey Hepburn |
| 2012-09-23 | With 78-Down, character commemorated in the answers to this puzzle's starred clues |
| 2012-04-09 | "My Fair Lady" lady |
| 2010-09-27 | Doolittle of "Pygmalion" |
| 2010-03-03 | Henry's tutee |
| 2010-01-14 | Henry's pupil |
| 2010-01-03 | Fictional Doolittle |
| 2009-07-14 | "My Fair Lady" role |
| 2009-05-24 | "My Fair Lady" lady |
| 2009-04-23 | "My Fair Lady" lady |
| 2007-10-22 | Doolittle of "My Fair Lady" |
| 2007-08-02 | "Uncle Tom's Cabin" woman |
| 2007-05-08 | Doolittle of fiction |
| 2006-01-21 | Cousin of Jane Eyre |
| 2005-09-05 | Henry's fair lady |
| 2005-08-02 | "My Fair Lady" character |
| 2004-04-26 | "My Fair Lady" lady |
| 2003-01-13 | Miss Doolittle of "My Fair Lady" |
| 2001-04-16 | "My Fair Lady" lady |
| 2000-03-26 | Henry's tutee |
| 1998-09-06 | 1964 role for Audrey |
| 1998-08-19 | She wants to "talk proper...like a lye-dy" |
| 1998-03-08 | Stowe character |
| 1997-06-18 | The "her" of "I've Grown Accustomed to Her Face" |
| 1996-07-02 | Professor Higgin's pupil |
| 1996-01-04 | Higgins's prodigy |
| 1994-10-24 | "My Fair Lady" miss |
| 1994-04-26 | "My Fair Lady" lady |