| 100% | HOLIDAY | 7 | "The ___," 2006 Christmas-themed rom-com starring Cameron Diaz and Kate Winslet |
| 70% | HOLIDAY | 7 | "The ___," 2006 American romantic comedy film starring Cameron Diaz and Kate Winslet |
| 69% | THEHOLIDAY | 10 | 2006 romcom starring Cameron Diaz and Kate Winslet |
| 68% | HOLIDAY | 7 | "The ___," 2006 romcom starring Cameron Diaz and Kate Winslet |
| 43% | OTHERWOMAN | 10 | The —, 2014 romcom starring Cameron Diaz and Leslie Mann |
| 42% | FLUSHEDAWAY | 11 | 2006 animated film starring the voice talent of Hugh Jackman and Kate Winslet |
| 42% | BOX | 3 | The —, 2009 mystery film starring Cameron Diaz and James Marsden |
| 42% | BOX | 3 | The —, 2009 film drama starring Cameron Diaz and James Marsden |
| 42% | WOMAN | 5 | "The Other ___," 2014 comedy starring Cameron Diaz and Leslie Mann |
| 40% | IRIS | 4 | Kate Winslet's character in the rom-com "The Holiday" |
| 40% | SEXTAPE | 7 | 2014 romcom starring Cameron Diaz and Jason Segel |
| 40% | OTHER | 5 | & 26A The —, 2014 romcom starring Cameron Diaz and Leslie Mann |
| 40% | THEBOX | 6 | 2009 mystery film starring Cameron Diaz and James Marsden |
| 39% | MYSISTERS | 9 | & 10A 2009 film drama starring Cameron Diaz and Abigail Breslin |
| 39% | BAD | 3 | & 14A 2011 film comedy starring Cameron Diaz and Justin Timberlake |
| 39% | STONE | 5 | "The Family ___," 2005 Christmas-themed rom-com starring starring an ensemble cast |
| 39% | BAD | 3 | "___ Teacher," 2011 romantic comedy film starring Cameron Diaz and Jason Segel |
| 38% | SKY | 3 | "Vanilla ___," 2001 sci-fi psychological thriller starring Cameron Diaz and Tom Cruise |
| 38% | ANY | 3 | "___ Given Sunday," 1999 sports drama film starring Cameron Diaz and Al Pacino |
| 38% | WHAT | 4 | "___ Happens in Vegas," 2008 romantic comedy film starring Cameron Diaz and Ashton Kutcher |
| 38% | ABOUTMARY | 9 | "There's Something ___," 1998 comedy starring Cameron Diaz and Ben Stiller: 2 wds. |
| 37% | OFNEWYORK | 9 | "Gangs ___," 2002 epic period drama film starring Cameron Diaz and Leonardo DiCaprio: 3 wds. |
| 37% | WERE | 4 | "While You ___ Sleeping," 1995 Christmas-themed rom-com starring Sandra Bullock |
| 36% | LOVEAGAIN | 9 | Rom-com starring 38-Across and Priyanka Chopra Jonas with the tagline "Destiny has a plan" (2 wds.) |
| 36% | IRIS | 4 | 2001 biopic featuring both Judi Dench and Kate Winslet in the title role |
| 35% | WINSLET | 7 | Kate, star of 2006's The Holiday |
| 35% | ANGELS | 6 | "Charlie's ___," 2000 action comedy film starring Cameron Diaz, Drew Barrymore and Lucy Liu |