Kyle Greenwood is a Canadian professional wrestler signed with AEW. He is best known for his work on the independent circuits, WWE, and AEW as Kyle O Rilley.
In 2005, Greenwood began working on the independent circuit as Kyle O Rilley. He spent a decade and rose to prominence on the independent circuit. He wrestled for several promotions, such as ECCW, ROH, PWG, and NJPW, where he won several championships. Rilley formed a team with Bobby Fish called reDRagon, which won several tag team championships. Rilley feuded with several top stars such as Adam Cole, Austin Aries, Christopher Daniels, Eddie Edwards, Marty Scurll, Matt Sydal, The Young Bucks, Wolves, and many more.
In August, Fish and Rilley attacked Drew McIntyre and joined forces with Adam Cole. After the event, the trio dubbed themselves as The Undisputed Era. At TakeOver WarGames, they defeated Team Sanity and Team AOP. In November, Fish and Rilley defeated Sanity to win the NXT Tag Team Championship. In January, Fish got injured, which allowed the group to activate the freebird rule. Cole and Rilley won the Dusty Rhodes Classic in 2019. At TakeOver WarGames, The Undisputed Era lost to Pete Dunne, Ricochet, and The War Raiders.
The Undisputed Era has the most reigning and is the longest-reigning champion in the company's history. Rilley has been an integral part of the stable's tag team division to win and keep championships. In June, they won their second NXT Tag Team Championship. After NXT TakeOver Toronto, they won their third NXT Tag Team Championship. In November, they entered WarGames and Survivor Series and lost. In 2020, the stable feuded with Imperium and lost at World's Collide event.
In February, the team lost the titles to Broserweights. Over the summer, Rilley assisted Adam Cole and feuded with Team McAfee. At WarGames, The Undisputed Era defeated Team McAfee. After the event, the stable began crumbling. Rilley began feuding with Finn Balor for the NXT Championship. In 2021, Adam Cole attacked Kyle O Rilley and ended the stable.
Over the year, Cole and Rilley reignited their feud from their ROH days. At TakeOver Stand and Deliver, Rilley defeated Cole in an unsanctioned match. At The Great American Bash, Rilley lost to Cole. The feud concluded when Rilley defeated Cole in a 2 out of 3 falls match at TakeOver 36. After the feud, Rilley spent the year teaming and feuding with Von Wagner. In December, Wagner defeated Rilley, and Rilley was released from the company.
In December, Rilley made his AEW debut by attacking Orange Cassidy. He aligned himself with Adam Cole, Bobby Fish, and The Young Buck. Rilley was last seen on Dynamite where The reDRagon won the battle royale to face the AEW World Tag Champions at Revolution.