Title History 2005 RAW Diva Search Winner; Career Highlights World Wrestling Entertainment – RAW Diva Search 2006: Summer 2005: Ashley Massaro won the 2005 RAW Diva Search after weeks of competition air LIVE on Monday Night RAW. ~~~Ashley Massaro was most recognized for giving out her legitimate cell phone number and took thousands of calls after. August 15, 2005 – RAW: Ashley Marraro was announced as the winner of the 2005 $250,000 RAW Diva Search. August 22, 2005 – RAW: Torrie and Candice debuted on RAW and turned heel, attacking DivaSearch winner Ashley Massaro. August 29, 2005 – RAW: Torrie and Candice tried to apologize to Ashley but it was all a set-up until Victoria attacked Ashley! September 5, 2005 – RAW: Ashley Massaro was a guest on Carlito’s Cabana, Carlito harassed her until Ric Flair made the save! ~~~Later on in a match: Torrie Wilson (w/Candice Michelle) defeated Ashley Massaro with help from Victoria. September 12, 2005 – RAW: Ashley Massaro was joined by the returning Trish Stratus in her battle with Torrie, Candice and Victoria! September 18, 2005 – Unforgiven: Trish Stratus and Ashley Massaro defeated Victoria and Torrie Wilson w/Candice Michelle. September 19, 2005 – RAW: Trish Stratus w/Ashley defeated Torrie Wilson w/Candice (Victoria attacked Trish afterwards). September 26, 2005 – RAW: Trish Stratus w/Ashley Massaro defeated Victoria when Torrie Wilson and Candice Michelle interfered. October 3, 2005 – WWE Homecoming: Trish and Ashley defeated Torrie and Candice and Victoria in a Handicap Bra and Panties match. October 17, 2005 – RAW: Torrie Wilson and Candice Michelle and Victoria beat Trish Stratus and Ashley Massaro and Mickie James. ~~~Mickie James wrestled most of the match trying to impress Trish, but ended up getting pinned by Torrie Wilson. October 21, 2005 – WWE Super Show: Trish Stratus and Ashley Massaro and Christy Hemme beat Torrie Wilson and Victoria and Melina. October 31, 2005 – RAW: Ashley Massaro (as a Dark Angel) participated in a special Divas Halloween Costume contest. World Wrestling Entertainment – Ashley Massaro: November 1, 2005 – Taboo Tuesday: Ashley Massaro participated in a Fulfill Your Fantasy Divas Battle Royal. ~~~Fans Chose Outfits for the Divas: 1) Cheerleader (25%), 2) Ligerie (43%), or 3) Leather and Lace (32%). November 14, 2005 – RAW Eddie Guerrero Tribute: Melina Perez (Latina Heat?) won a Nine-Diva Inter-promotional Battle Royal! ~~~Included: Trish Stratus, Mickie James, Ashley Massaro, Maria, Candice, Christy Hemme, Jillian Hall, Victoria and Melina. November 28, 2005 – RAW: Trish Stratus and Mickie James and Ashley Massaro beat Victoria and Candice Michelle and Torrie Wilson. December 15, 2005: Ashley Massaro of WWE had a six-page layout in the January issue of Maxim Magazine. December 19, 2005 – RAW from Afganistan: Candice Michelle and Maria Kanellis defeated Trish Stratus and Ashley Massaro. January 8, 2006 – New Years Revolution: Ashley Massaro won a Vince McMahon-booked Bra and Panties Gauntlet Match. ~~~Maria Kanellis stripped Candice Michelle | Maria stripped Torrie Wilson | Victoria stripped Maria | Ashley stripped Victoria. January 9, 2006 – RAW: Ashley Massaro defeated Trish Stratus by DQ when Mickie James attacked Ashley! (to protect Trish). January 16, 2006 – RAW: Victoria and Candice and Torrie beat Trish and Mickie and Ashley when Mickie snapped and attacked Ashley! January 23, 2006 – RAW: Trish Stratus and Ashley Massaro defeated Victoria and Candice Michelle w/Torrie Wilson and Chloe. ~~~Ashley Massaro performed a picture perfect cross body off the top rope onto Victoria to get the victory. ~~~Ashley Massaro celebrated by hugging Trish Stratus, causing a jealous Mickie James to run down and attack Ashley!!! January 29, 2006 – Royal Rumble: Mickie Jamies defeated Ashley Massaro with Trish Stratus as the guest referee. January 30, 2006 – RAW: Mickie James had “Celebration of Trish Stratus” in the hopes that Trish would say “I Love You, too”. ~~~Ashley Massaro showed up and said Mickie James was a PSYCHO, so Mickie freaked out and attacked Ashley Massaro. ~~~Trish Stratus pulled Ashley Massaro off of Mickie James and held he back as Mickie delivered a spin kick to Ashley! ~~~Of course, Mickie James took this as a sign of affection from Trish Stratus and concluded that Trish cared about her. January 31, 2006: Ashley Massaro’s bra and panties from New Year’s Revolution were auctioned off with a Final Bid of 1502.50 (US). February 6, 2006 – RAW: Ashley Massaro defeated Mickie James with Trish Stratus as the guest referee. February 13, 2006 – RAW: Ashley Massaro defeated Torrie Wilson w/Candice Michelle. February 20, 2006 – RAW: Ashley Massaro suffered a broken leg taking her bump out of the ring in a Women’s Battle Royal. February 22, 2006: Ashley Massaro ended up undergoing surgery to have a plate, one screw and staples put in her leg. ~~~She suffered a large fracture that went around the bone twice, like a corkscrew, plus there was a loose piece of bone. March 20, 2006 – RAW: Mickie James kidnappned the injured Ashley Massaro to lure Trish to the ring and gave her a DDT! World Wrestling Entertainment – Ashley Massaro on SmackDown: June 2, 2006 – SmackDown: Ashley Massaro debuted on SmackDown to join commentary during a Jillian vs Kristal match. June 9, 2006 – SmackDown: Ashley Massaro beat Kristal Marshall, Jillian Hall and Michelle McCool in a Bikini Contest! June 16, 2006 – SmackDown: Ashley Massaro had a confrontation with Michelle McCool who declined a 1-on-1 Bikini Contest. June 30, 2006 – SmackDown: Kristal Marshall interviewed Ashley Massaro talking about the upcoming 2006 WWE Diva Search. ~~~Ashley Massaro said how fun it was and she made so many friends in the Top 10, and Kristal shouted “I placed 4th. BITCH!”. July 14, 2006 – SmackDown: Kristal Marshall and Michelle McCool got into a backstage catfight with Ashley Massaro and Jillian Hall. July 15, 2006 – SNME: Ashley Massaro participated in a special WWE Divas Mechanical Bull Riding contest (won by Michelle). July 21, 2006 – SmackDown: Ashley Massaro and Jillian Hall defeated Kristal Marshall and Jillian Hall. July 23, 2006 – Great American Bash: Ashley Massaro beat Kristal Marshall and Jillian Hall and Michelle McCool (Bra and Panties). August 4, 2006 – SmackDown: Kristal Marshall pinned Ashley Massaro by pulling on her tights for leverage. ~~~Ashley Massaro suffered a broken hand during this match and she will likely need a cast for about four weeks. August 11, 2006 – SmackDown: Luke Perry (of 90210 Fame) was there and Ashley and Kristal argued over who should talk to him. October 10, 2006 – ECW on Sci Fi: Ashley Massaro participated in a series of Extreme Strip Poker segments with Divas from all three brands. October 6, 2006 – SmackDown: Michelle McCool (w/her Teacher’s Pets) defeated Ashley Massaro (London and Kendrick). October 8, 2006 – No Mercy: Paul London and Brian Kendrick w/Ashley defeated Idol Stevens and K.C. James w/Michelle McCool. October 20, 2006 – SmackDown: The Miz hosted a Diva Dance off with the SmackDown Divas judged by Nick and Aaron Carter. October 27, 2006 – SmackDown: Ashley (as a Ferrie) participated in a Diva’s “Trick or Treat Battle Royal (won by Kristal). November 3, 2006 – SmackDown: Paul London and Brian Kendrick w/Ashley defeated Idol Stevens and K.C. James w/Michelle McCool. November 17, 2006 – SmackDown: William Regal defeated Paul London w/Ashley Massaro (who suffered an implant injury). ~~~Paul London took an unfortunate bump out of the ring and landed directly onto Ashley Massaro’s inflated chest! December 17, 2006 – Armageddon: Ashley Massaro vs Kristal Marshall vs Jillian Hall vs Layla El in a Ligerie Contest. ~~~Big Dick Johnson was there playing Santa Clause and declared all four girls the winner and then stripped and danced. December 22, 2006 – SmackDown: Ashley Massaro and Layla El defeated Kristal Marshall and Jillian Hall. World Wrestling Entertainment – (SmackDown) Playboy Bunny: January 5, 2007 – SmackDown: Ashley Massaro defeated Jillian Hall in a Divas Match. January 26, 2007 – SmackDown: MNM (Mercury and Nitro and Melina) defeated Brian Kendrick and Paul London and Ashley Massaro. February 2, 2007 – SmackDown: Ashley Massaro vs Jillian Hall vs Kristal Marshall had a Bikini Contest hosted by JBL! February 16, 2007 – SmackDown: Ashley Massaro unvailed the cover of Playboy which coincidentally features her naked inside. February 18, 2007 – No Way Out: Ashley Massaro participated in a Divas Talent Contest hosted by Mike “The Miz” Mizanin. ~~~Ashley Massaro came out last and took off her shirt to reveal Playboy logos painted on her bare breasts. March 2, 2007 – SmackDown: Ashley Massaro defeated Jillian Hall in a Divas match. March 5, 2007 – RAW: After a successful title defense, Melina Perez confronted Ashley Massaro, who shoved Melina on her ass! March 9, 2007 – SmackDown: Mike “The Miz” Mizanin debuts his Miz TV segment interviewing Ashley Massaro and Melina Perez. March 16, 2007 – SmackDown: MNM (Mercury and Nitro and Melina) defeated Brian Kendrick and Paul London and Ashley Massaro. March 23, 2007 – SmackDown: Brian Kendrick and Paul London w/Ashley Massaro defeated MNM (Mercury and Nitro w/Melina). March 26, 2007 – RAW: Ashley Massaro and Torrie Wilson and Candice Michelle defeated Melina Perez and Victoria and Jillian Hall. March 30, 2007 – SmackDown: Ashley and Mickie and Maria and Candice and Torrie beat Melina and Victoria and Jillian and Kristal and Michelle. April 1, 2007 – Wrestlemania 23: Melina Perez defeated Ashley Massaro in a Lumberjills match to retain the WWE Women’s title. April 13, 2007 – SmackDown: Jillian Hall attacked and “injured” Ashley Massaro thus writing her out of the storylines. World Wrestling Entertainment – Ashley Massaro: World Wrestling Entertainment – I’m a Survivor: August 31, 2007 – SmackDown: Ashley was shown preparing for her opportunity to appear on the reality show “Survivor”. When the program finally aired, Ashley Massaro did so poorly that she was the second person voted off the show. World Wrestling Entertainment – Ashley Massaro (What’s Up [Insert City]!): January 7, 2008 – RAW ROULETTE: Ashley Massaro returned to RAW and won the 5-WAY WWE Divas Pillow Fight! January 14, 2008 – RAW: Melina Perez and Jillian Hall and Beth Phoenix beat Ashley Massaro and Mickie James and Maria Kanellis. January 21, 2008 – RAW: Ashley Massaro tried to talk to Maria about posing for Playboy but Santino Marella interrupted. January 27, 2008 – Royal Rumble: Ashley Massara told Maria Kanellis that Hugh Heffner himself wanted her to pose for Playboy. ~~~Santino Marella interrupted and objected to the proposal and let Big Dick Johnson do a strip tease for the fans instead! January 28, 2008 – RAW: Beth Phoenix and Jillian Hall defeated Mickie James and Ashley Massaro in a Divas Tag match. February 17, 2008 – No Way Out: WWE Divas Ashley Massaro and Maria Kanellis attended a party at the Playboy Mansion. World Wrestling Entertainment – Ashley Massaro (The Road To WrestleMania 24): March 24, 2008 – RAW: Maria vs. Melina ended in a No Contest when Ashley Massaro randomly interfered in the match. ~~~Santino Marella came down univited so Jerry “The King” Lawler got out of his seat and knocked Santino out of the ring! ~~~Santino Marella and Beth Phoenix and Melina Perez defeated Maria Kanellis and Ashley Massaro and Jerry “The King” Lawler. March 30, 2008 – WrestleMania 24: Beth Phoenix and Melina beat Maria and Ashley Massaro in a BunnyMania Lumberjill Match . ~~~LUMBERJILLS: Mickie James, Michelle McCool, Eve Torres, Kelly Kelly, Jillian Hall, Victoria, Cherry, Maryse, Layla El. World Wrestling Entertainment – Ashley Massaro (A Pink Slip Waiting To Happen): April 14, 2008 – RAW: Melina Perez and Jillian Hall defeated Maria Kanellis and Ashley Massaro in a match taped for HEAT. April 21, 2008 – RAW: Mickie James celebrated her victory with the “good” divas; Maria, Ashley, Michelle, Kelly, and Cherry. ~~~Beth Phoenix – backed up by Melina, Victoria, Natalya, and Jillian – crashed the party and started a huge Divas brawl! April 27, 2008 – Backlash: Beth Phoenix’s Team of heel Divas defeated Mickie James’ Team of babyface Divas in a 5-on-5. ~~~Beth and Melina and Jillian and Victoria and Natalya and Layla beat Mickie and Maria and Ashley and Michelle and Cherry and Kelly. April 28, 2008 – RAW: Mickie James’ Team of babyface Divas defeated Beth Phoenix’s Team of heel Divas in a rematch. ~~~Mickie and Maria and Ashley and Michelle and Cherry and Kelly beat Beth and Melina and Jillian and Victoria and Natalya and Layla . July 2, 2008: Ashley Massaro announced she was “ leaving WWE to care for her ill seven-year-old daughter as a single mom“. October 2009: Ashley Massaro travelled to Mexico City for a couple of days to host the Playboy Latin America anniversary party. January 31, 2015 – PWS: Mike Del w Ashley Massaro defeated Trent Barreta.