| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| "Shakespeare in Love" & "Glee" | Gwyneth Paltrow | $600 | J | I'VE WON AN OSCAR & AN EMMY | 2021-03-10 | #8353 | |
| 1998 for "Shakespeare in Love" | Gwyneth Paltrow | $400 | DJ | BEST ACTRESS OSCAR WINNERS | 2001-12-07 | #3975 | |
| Hilary Swank won in 2000 for pretending to be a boy; this actress won for the same thing the year before | Gwyneth Paltrow | $100 | J | OSCAR, OSCAR | 2000-10-27 | #3715 |