The Owner's Cup was an annual Lords of Pain Wrestling tournament with the premise of the winner receiving the Owner's Cup trophy and a special guaranteed reward. The tournament featured contestants from both of LPW's brands, Insanity and Inferno.
In each round of the tournament, invited e-wrestlers must write a promo under the requirements and restrictions given by the LPW owner (word counts, settings, guest appearances, and other random hilarity). Unlike LPW's usual "Voting & Promo" method in deciding winners, Owner's Cup matches are soley determined by the LPW owner/president. Whoever the LPW authority figure believes had the strongest promo while meeting the required conditions advances to the next round.
Created in 2005 by PWA owner, Villiano 187, the Owner's Cup was announced to be an annual tournament to crown a new number one contender. Participants were first asked if they wanted to be apart of the tournament, then selected by Villiano.
In the first two years of the Owner's Cup, the winner of the tournament received a guaranteed title match for his brand's world championship, either the PWA World Heavyweight Championship or the PWA International Heavyweight Championship. In addition, the Owner's Cup winner could also choose the match at a time and place of his choosing within one year of winning the tournament.
In 2007, the Owner's Cup tradition continued under new management. The 2007 tournament featured a couple of different twists. Instead of a guaranteed title shot, the winner would receive the unique opportunity to be head booker of his brand's show for one night. Also, instead of selecting the participants, tournament participants were invited. The first round was contested under Royal Rumble rules, where the last 16 men would advance to the second round of the tournament, while also determining the tournament seeding.
In 2005, Jaro became the first man to win the Owner's Cup when he defeated Pen in the finals. While the Owner's Cup tournament was going on, Jaro also won the vacant International Heavyweight Championship and thus had no need to use his guaranteed title shot. At One Way Ticket (the final Pyromania pay-per-view before Altered Reality III), Jaro announced that he would be using his guaranteed title shot in the Martinez Cup match against Pen for the PWA World Heavyweight Champion. Days before the match however, Jaro was fired by PWA management and forced to relinquish his guaranteed title shot.
In 2006, Wevv Mang became the second man to win the Owner's Cup after he defeated Sheepster at Altered Reality III. Mang cashed in his title shot at Inferno 11.2, where was defeated by D. Hammond Samuels for the International Heavyweight Championship.
In 2007, the Owner's Cup took place in Anaheim, California. The tournament kicked off with a 36-man Royal Rumble, where the top 15 competitors remaining in the ring advanced to the tournament portion. The winner of the Royal Rumble match was Tromboner Man, who received a next round bye.
Due to the California wildfires, the semifinals were postponed and merged with the finals. In a Fatal Four-way match to determine the winner, The Rik defeated Tromboner Man, N'itomniskittel, and Peter Saint to become the 2007 Owner's Cup Champion. The Rik was awarded the opportunity to be Inferno General Manager for one night, but he left the promotion before he could take advantage.
- Main article: Owner's Cup (2009)
In 2008, the Owner's Cup took a hiatus and was replaced by the Winner Takes All tournament.
On April 10, 2009, Villiano 187 announced that the Owner's Cup would be returning under his production. For the first time the tournament was expanded to 32 superstars, with 16 superstars from each of LPW's brands, Insanity and Inferno, having the ability to accept an invitation. The winner of the tournament will receive a guaranteed title match with the choice of either the LPW World Heavyweight Championship or LPW International Heavyweight Championship.
- Main article: Owner's Cup (2011)
Due to popular demand, the Owner's Cup will return, once again under his production, announced on October 7, 2011, with 32 men set to compete.