[1] As part of his controversial in-ring persona, heavily influenced by "Ravishing" Rick Rude and Shawn Michaels, he has wrestled in a considerable number of mixed and intergender matches with numerous female wrestlers.

The brawl included a filing cabinet, an ironing board, a ladder, and smashing beer bottles on their heads, was taped on video and widely distributed in the local Montreal-area.

[3] In early 1999, Eddy joined with PCP Crazy F’N Manny and Nixon Stratus to form the World Wrestling Syndicate (WWS) and held their first show, Blood, Sweat & Beers '99 at "Wally's Pub" on June 17, 1999.

Due to the ceiling being so low, this space could easily be converted into a makeshift wrestling ring by attaching ropes to the pillars and laying down mats taped together.

After Eleftheriou formed a partnership with Carol Cox's Wild Rose Productions, a Montreal-based adult entertainment internet company, the promotion began holding events at the Club Le Medley.

On November 21, Eddy appeared at the IWS's second Medley show, Born to Bleed '01, pinning PCP Crazy F’N Manny in the main event after a leaping frog splash off the balcony.

[5] In June 2002, Eddy faced former World Wrestling Federation star Brutus "The Barber" Beefcake in the 2nd round of the tournament and suffered a concussion during the match.

Initially introduced performing a lap dance on Zandig's wife, he later went on to defeat Ian Knoxx in a "Thumbtack & Carpet Strip" match in the opening rounds.

[1] Inviting him back for CZW's High Stakes on September 11, SeXXXy Eddy defeated Kevin Steen, El Generico and eXeSs in a four-way match.

On June 12, Eddy appeared in the main event of the IWS 5th anniversary show V teaming with the Green Phantom in a death match against Arsenal and Evil Ninja.

On September 25, Eddy appeared in the co-main event at Freedom to Fight against eXeSs and IWS Heavyweight Champion "Mr.Wrestling" Kevin Steen in a triple threat match.

[12] On October 30, Eddy made his first appearance for Jersey All Pro Wrestling losing to El Generico in a four-way match with eXeSs and Beef Wellington.

At the New Year's Madness supercard on January 22, he defeated Beef Wellington, Damian, Kid Kamikaze, Mr. X-TreeM and Hell Storm in a six-way match.

Losing to Kevin Steen at a show for Pro Wrestling Guerrilla on May 13, the following night in CZW he and "Spyder" Nate Webb defeated Blackout (Ruckus and Eddie Kingston).

On August 26, Eddy lost to Beef Wellington in a four-way match with El Generico and Kevin Steen at another show for UWA Hardcore Wrestling.

Entering the Chikara 2006 World Grand Prix Tag Tournament, SeXXXy Eddy and "Mr.Wrestling" Kevin Steen lost to Arik Cannon and Jigsaw in the opening rounds on February 26.

At an event for CWA Montreal, he and Necro Butcher lost to The Alliance of Violence ("Strongman" Gino Martino and Pierre "The Beast" Vachon) in an American Hardcore Frenzy match on April 8.

SeXXXy Eddy also made a 2-day appearance for IWA Mid-South entering as the only male wrestler in the first annual Queen of the Death Match Tournament on November 3.

[1][17] On November 10, SeXXXy Eddy and Beef Wellington lost to "Up in Smoke" (Cheech and Cloudy) at an MXW show in Albany, New York for promoter and former ECW announcer Joel Gertner.

That same month, Eddy and the Green Phantom formed "Scarred and SeXXXy" later winning the IWS Tag Team titles from The Hardcore Ninjaz in a Montreal Death match on March 24.

During the next month, he appeared in New York's NWA Upstate and Oshawa, Ontario's Motor City Wrestling before losing the titles back to The Hardcore Ninjaz in a 3-way match with "The Super Smash Brothers" (Player Uno and Stupefied) on April 28.

They failed to regain the titles in a rematch which included "Hi-5" (Beef Wellington and Kid Kamikaze) on May 26 and again in a No Ropes Barbed Wire match on June 16 and broke up shortly after.

On October 12, he entered the ALF's Amazones et Titans mixed tag team tournament with Vanessa Kraven, however they fought to a time limit draw with eXeSs and Kacey Diamond in the opening rounds.

On November 2, Eddy defeated "The Prince of Persia" Rahim Ali in Cornwall; and later that night, lost to Jeremy Prophet in a match for the CWA Internet-TV Championship.

On December 1, SeXXXy Eddy and Scotty Vortekz defeated UltraMantis Black in a triple threat match to advance to the finals of the Deathmatch Tournament at 2007 IWA Deep South Carnage Cup in Pulaski, Tennessee.

[1][19] That same night, although Eddy was absent from the IWS, his valet Hottie Holly distracted LuFisto in a death match against PCP Crazy F'N Manny in order for 2.0 (Jagged and Shane Matthews) to attack her from behind.

On December 5, Eddy lost to NWF Heavyweight Champion Kryss Thorn; and the following night, he defeated Razz Mansour in a match for Great Canadian Wrestling in Oshawa, Ontario.

On February 23, he and Karnage (with Andy Rossetti) lost to "Aftershock" (Damian and Drake Styles) in a match for the NWA Canadian Tag Team Championship at CWA: The Return.

On March 1, Eddy appeared at IWA-Mid South's 500th Anniversary Show in Joliet, Illinois and participated in an 8-man TLC Open Contract match which involved: Ash, Ruckus, Mickie Knuckles, Devon Moore, Brandon Thomaselli, Jaysin Strife and "Diehard" Dustin Lee.

On July 19, he lost to Kevin Steen and 2.0 (Jagged and Shane Matthews) in a 6-man tag team match with Beef Wellington and Evil Ninja in the main event at IWS Summer Slaughter.