On May 25, 2019, at Double or Nothing, Uno and Grayson were repackaged and made their surprise debut as The Dark Order. After Best Friends defeated Angélico and Jack Evans, Uno and Grayson appeared ringside after the lights went out, and attacked everyone alongside their masked henchmen. On July 13, at Fight for the Fallen, they made their AEW in-ring debut in a three-way tag team match defeating Angélico, Evans and Jurassic Express, advancing to All Out for an opportunity at a first round bye in the AEW World Tag Team Championship tournament. On August 31, at All Out, they defeated Best Friends to receive a first round bye in the AEW World Tag Team Championship tournament. They were unsuccessful in the tournament, losing to eventual winners SoCal Uncensored on the October 23 episode of Dynamite. On November 20, the first of a series of Dark Order vignettes began airing, and in doing so, introduced the spokesman for the stable, who communicated to Alex Reynolds through a hotel television. Then, John Silver and Alex Reynolds joined the Dark Order. On the January 1, 2020 episode of Dynamite, The Exalted One then was revealed as the Dark Order's mysterious off-screen leader. The stable first feud was with SoCal Uncensored when the Order tried to recruit Christopher Daniels following his loss to Sammy Guevara. During the following weeks, The Dark Order faced Socal Uncensored including a victory at Revolution, where Uno and Grayson defeated Kazarian and Sky in a tag team match. On the March 18, 2020 episode of Dynamite, Brodie Lee made his AEW debut and was revealed as The Exalted One and the leader of The Dark Order, beating up Daniels and Kazarian. Then, Lee would have several squashes against other wrestlers. Also, on the April 22, 2020 episode of Dynamite, Preston Vance joined the stable as 10. On June 5, it was revealed that Alan Angels had been recruited as a new member of the Dark Order under the moniker of 5. He would later debut on the June 9, 2020 episode of AEW Dark. In May, Colt Cabana began a losing streak as Brodie Lee tried to recruit him into The Dark Order. On the June 10 episode of Dynamite, after Cabana lost to Sammy Guevara, Lee came out to help Cabana to his feet and once again offer him a spot in the Dark Order. Later on in the night, Cabana was seen heading into Lee’s office. The following week, Cabana was handed an envelope by Lee that stated they will team together against Joey Janela and Sonny Kiss. At the same time, Brodie Lee extended a hand to Anna Jay after her loss to Abadon. Cabana and Lee would defeat Janela and Kiss after Cabana got the pin on Janela. Over the next few weeks, Cabana would begin a winning streak teaming with members of the Dark Order as he was slowly recruited into the group over time. Anna Jay would later make her first appearance alongside the Dark Order on the July 29th episode of Dynamite.
Independent circuit (2019)
Following Double or Nothing, Uno and Grayson were booked for some independent shows, usually against AEW contracted wrestlers, before the premiere of Dynamite in October 2019. This began at Pro Wrestling Guerilla's Sixteen, on July 26, marking their first appearance in the company since 2013, when they were known as the Super Smash Brothers. They defeated Best Friends by disqualification, when Trent hit a low blow in retaliation for the Dark Order doing the same when the referee was down. On August 7, at an Oriental Wrestling Entertainment show in Toronto, they defeated Strong Hearts. The next day, they appeared at a Progress Wrestling show in the same city, but were defeated by Aussie Open, in a three-way match, also involving The Butcher and The Blade.
