Diaz's only film of 2007 was “Shrek the Third”, the third instalment in the Shrek franchise, which also featured Justin Timberlake in a supporting role. Although the film was met with mixed reviews from critics, it grossed $798 million worldwide. The same year, Diaz also voiced Princess Fiona in a thirty-minute Christmas special, directed by Gary Trousdale.

Her next film “What Happens in Vegas” opposite Ashton Kutcher was a romantic comedy by Tom Vaughan. Diaz and Kutcher portrayed two strangers who awaken together to discover they have gotten married following a night in which they won a huge jackpot after playing the other's quarter. The film was partly shot in New York City and included the locations 19 Old Fulton Street in Brooklyn, the New York County Supreme Court at 60 Centre Street, the offices at 19 Gramercy Park and Pearl Street between Plymouth Street and Water Street in Brooklyn.

In 2009, she starred in “My Sister's Keeper” and “The Box”. Based on Jodi Picoult's novel of the same name, “My Sister's Keeper” was released to mixed reviews in June 2009. In the drama, Diaz plays a former lawyer and mother of three, one of whom is dying of leukemia. A moderate commercial success, it grossed $95 million worldwide, mostly from its domestic run. Set in 1976, “The Box”, written and directed by Richard Kelly, stars Diaz and James Marsden as a couple who receive a box from a mysterious man who offers them one million dollars if they press the button sealed within the dome on top of a box, knowing that someone, somewhere, will die from it. Critical response towards the psychological horror film was mixed, and, though having grossed its budget back, was considered a financial disappointment.

In 2010, Diaz reprised her voice role of Princess Fiona in “Shrek Forever After”, the fourth instalment in the Shrek series. Although the film opened to mixed reviews from critics, it grossed a worldwide total of over $752 million and became the fifth top-grossing films released that year. Also in 2010, Diaz reunited with her “Vanilla Sky” co-star Tom Cruise in the action-comedy film “Knight and Day”. In it, Diaz plays a classic car restorer who unwittingly gets caught up with the eccentric secret agent Roy Miller, played by Cruise, who is on the run from the Secret Service.

In 2011, Cameron Diaz was cast as Lenore Case, a journalist, in the remake of the 1940s film “The Green Hornet”. Directed by Michel Gondry, Diaz starred alongside Seth Rogen, Jay Chou, and Christoph Waltz in the superhero action-comedy film. The same year, she played opposite Justin Timberlake and Jason Segel in Jake Kasdan's adult comedy “Bad Teacher”. In the film, Diaz plays an immoral, gold-digging Chicago-area middle school teacher at the fictional John Adams Middle School who curses at her students, drinks heavily, and smokes marijuana.

In 2012, Diaz was cast in “What to Expect When You're Expecting”, directed by Kirk Jones and based on the pregnancy guide of the same name. Diaz, who filmed her scenes in a two-week period, portrays Jules Baxter, a contestant on a celebrity dance show and a host to a weight-loss fitness show, who becomes pregnant with her dance partner's baby. Upon release, the ensemble comedy received mostly negative reviews, but became a moderate commercial success with a worldwide gross of $84.4 million. Diaz's other film that year was “Gambit”, a remake of the 1966 film of the same name directed by Michael Hoffman and scripted by Joel and Ethan Coen. The film received overwhelmingly negative reviews, and performed poorly at the box office, grossing only $10 million internationally.

Diaz's only film project of 2013 was Ridley Scott's “The Counselor”, co-starring Michael Fassbender, Javier Bardem, Penélope Cruz, and Brad Pitt. In the thriller about greed, death, the primal instincts of humans and their consequences, Diaz plays a pathological liar and a sociopath, an immigrant who is now living the high-life after escaping a sordid past as an exotic dancer. While the film's reception was negative, her performance was praised as one of her best in recent years.

Diaz's first film of 2014 was the romantic revenge comedy “The Other Woman” opposite Nikolaj Coster-Waldau, Leslie Mann, and Kate Upton. The film was shot in New York and included the locations; the Conservatory Water and The Mall in Central Park, the office building at 1 New York Plaza in Water Street, the rooftop bar at The James Hotel in Grand Street, the apartment building at 104 Greene Street in SoHo, the Monkey Bar at 60 East 54th Street, the Stone Street Tavern at 52 Stone Street, the Barbuto Restaurant at 775 Washington Street and the STK Restaurant at 1114 6th Avenue.

Her next film release in 2014 was the comedy “Sex Tape”, in which she starred with Jason Segel as a married couple waking up to discover that a sex tape they had made went missing, leading to a frantic search for its whereabouts. The role required Diaz to perform multiple scenes of nudity.

Her final film that year was the film adaptation “Annie”, co-starring Quvenzhané Wallis, Jamie Foxx, and Rose Byrne. She took on the role of Miss Colleen Hannigan, the cruel control freak of the foster home where the titular character resides. Upon its December premiere, “Annie” made $133 million worldwide, with Diaz's performance garnering polarised reviews; critics praising her effort, but ultimately calling it too vampy as well as strident and obnoxious. The film was shot in New York and included the locations; the apartment building at 366 West 127th Street in Harlem, the office building at 250 Greenwich Street, the Beacon Theatre at 2124 Broadway, at the corner of West 4th Street and West 12th Street, the Guggenheim Museum at 1071 5th Avenue, Cafe Cluny at 284 West 12th Street, and Diaz’s final scene outside East Harlem School at 309 East 103rd Street between 1st and 2nd Avenues in Harlem.

Diaz decided to take a break from acting following the release of “Annie” and confirmed her retirement from it the following March.