| 100% | KATES | 5 | Middleton and Winslet |
| 63% | KATES | 5 | Beckinsale and Winslet |
| 60% | KATES | 5 | Middleton and Moss |
| 54% | KATES | 5 | Winslet and Hudson |
| 53% | COLEADS | 7 | Dench and Winslet, as 91 Across |
| 52% | IRISMURDOCH | 11 | Dench and Winslet, in a 2001 biopic |
| 52% | KATE | 4 | Upton, Winslet, Middleton |
| 51% | TITANIC | 7 | DiCaprio and Winslet were on this sinking ship |
| 50% | KATE | 4 | Winslet of “Titanic” and “Revolutionary Road” |
| 49% | KATE | 4 | ___ Middleton, Duchess of Cornwall and Cambridge |
| 47% | AUNT | 4 | Kate Middleton, to Archie and Lilibet |
| 47% | IRIS | 4 | Murdoch portrayed by Winslet and Dench |
| 45% | TITANIC | 7 | 1997 drama starring Kate Winslet and Leonardo DiCaprio |
| 45% | THEHOLIDAY | 10 | 2006 romcom starring Cameron Diaz and Kate Winslet |
| 45% | CARNAGE | 7 | Black comedy starring Kate Winslet and 28-Across |
| 43% | WHEEL | 5 | "Wonder ___" (2017 film starring Justin Timberlake and Kate Winslet) |
| 43% | TITANIC | 7 | 1997 film drama starring Leonardo DiCaprio and Kate Winslet |
| 43% | ENIGMA | 6 | 2001 film drama starring Dougray Scott and Kate Winslet |
| 43% | IRIS | 4 | Kate Winslet movie about, and titled for, author Murdoch |
| 43% | HOLIDAY | 7 | "The ___," 2006 romcom starring Cameron Diaz and Kate Winslet |
| 43% | KATE | 4 | ___ Middleton and Prince William, whose wedding at Westminster Abbey in London made headlines in 2011 |
| 43% | AFAIRQUARREL | 12 | Thomas Middleton and William Rowley tragicomedy published in 1617 whose characters include Lady Ager |
| 42% | IRIS | 4 | Author Murdoch played onscreen by Kate Winslet and Judi Dench |
| 42% | CHANGELING | 10 | The —, Jacobean tragedy by Thomas Middleton and William Rowley featuring the characters Alsemero and Jasperino |
| 41% | SENSE | 5 | "___ & Sensibility," a 1995 romantic drama starring Emma Thompson and Kate Winslet |
| 39% | HOLIDAY | 7 | "The ___," 2006 American romantic comedy film starring Cameron Diaz and Kate Winslet |
| 39% | IRIS | 4 | 2001 movie for which Kate Winslet and 37-Down were Oscar-nominated |
| 39% | HOLIDAY | 7 | "The ___," 2006 Christmas-themed rom-com starring Cameron Diaz and Kate Winslet |
| 38% | KATE | 4 | ___ Winslet and Leonardo Dicaprio, "Titanic" actors who have starred in multiple rom-coms together |
| 38% | IRIS | 4 | 2001 film in which Kate Winslet and Judi Dench played the title role |