While wrestling for Chicago-based All American Wrestling (AAW), Gargano ran into Colt Cabana, who suggested he get in touch with former Ring of Honor booker Gabe Sapolsky, who was looking for talent for the Dragon Gate USA and Evolve Wrestling promotions, and tell him that Cabana sent him. Gargano received a tryout match for Dragon Gate USA on July 25, 2009, at the tapings of the Enter the Dragon pay-per-view, wrestling in an eight-way elimination dark match, which was won by Lince Dorado. On September 6 Gargano wrestled in another dark match at tapings of Untouchable, where he defeated Arik Cannon, Flip Kendrick, Hallowicked, Louis Lyndon, Prince Mustafa Ali, Shiima Xion and the Great Malaki in an eight-way elimination match. On November 28 at Freedom Fight, Gargano made his pay-per-view debut by entering the tournament to crown the first Open the Freedom Gate Champion, but was eliminated in the first round in a six-way match with Hallowicked, Lince Dorado, Matt Jackson, Nick Jackson and the winner of the match, Gran Akuma. On January 16, 2010, Gargano participated in Evolve Wrestling's first show, defeating Chris Dickinson in a singles match. Seven days later at Dragon Gate USA's fourth PPV, Fearless, Gargano wrestled in another dark match, losing to Kyle O'Reilly in a six-way match. In May 2010 Gargano signed a contract with Dragon Gate USA. On July 24, 2010, at Enter the Dragon 2010, Gargano wrestled his first singles match in Dragon Gate USA, losing to Cima, a founding father of Dragon Gate, the parent company of Dragon Gate USA. At the following event on September 25, Gargano was defeated by Chuck Taylor in a four-way match, which also included Drake Younger and Rich Swann. The following day Gargano offered himself to Cima's Warriors International stable, before defeating Drake Younger in a singles match. On October 29 at Dragon Gate USA's first live pay-per-view, Bushido: Code of the Warrior, Gargano wrestled in a four-way match, which was won by Chuck Taylor and also included Arik Cannon and Ricochet. After Taylor turned down an offer from Cima to join his Warriors International stable, Gargano offered himself to Cima, but was turned down. Gargano confronted Cima again after his match, offering himself to Warriors International, before attacking him and his stablemate Ricochet, along with Chuck Taylor and Rich Swann. The three formed their own stable called Ronin. At the following day's tapings of Freedom Fight 2010, Ronin defeated Austin Aries, Genki Horiguchi and Ricochet in a six-man tag team match.
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