- 2005 RAW Diva Search Winner;
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]!):
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.