O'Reilly appeared at NWA: Extreme Canadian Championship Wrestling (ECCW)'s television tapings on December 23, 2005, where he and Tony Tisoy lost to Wrathchild and Killswitch. In January 2006, O'Reilly was in the main event of ECCW's tenth anniversary show, teaming with Fast Freddy Funk and Kurt Sterling to defeat Michelle Starr, Johnny Canuck and Vance Nevada. O'Reilly graduated from ECCW's House of Pain Wrestling School on May 29, 2006. At the graduation show, O'Reilly pinned his trainer Aaron Idol. He continued to appear in ECCW throughout the remainder of 2006 and early 2007. In March 2007, O'Reilly began a feud with Sid Sylum, losing to him in a "European Rounds" match on March 2, before he teamed with Veronika Vice to defeat Sylum and Nikki Matthews in a mixed tag team match the following night. On March 30, O'Reilly defeated Sylum in an "I Quit" match to end the feud.
In June 2007, O'Reilly entered the Pacific Cup tournament, where he faced Tony Kozina and Scotty Mac in the final and was victorious. On July 21, O'Reilly defeated Ice to win the NWA Canadian Junior Heavyweight Championship. He lost the championship back to Ice just six days later. The following month, on August 18, O'Reilly once again defeated Ice to win the NWA Canadian Junior Heavyweight Championship for the second time, but lost it back to Ice again the same day. In a rematch on August 24, the match ended in a double pin, causing the championship to be vacated. As a result, O'Reilly and Ice competed in a best of five series to determine the new champion. O'Reilly defeated Ice in the first match of the series on November 16, but Ice won the second to tie the series at one all. O'Reilly won the third match, but Ice won the fourth, a street fight. In the rubber match on December 28, O'Reilly defeated Ice in a Last Man Standing match to win the championship for the third time.
In 2008, O'Reilly attempted to win the Pacific Cup for the second year in a row, but was unsuccessful. He defeated Halo and Azeem en route to the final, a three-way elimination match against Billy Suede and El Phantasmo, but was the first man eliminated. In April 2009, O'Reilly and 19 other wrestlers took part in ECCW's Wrestling With Hunger marathon show, where he wrestled almost 40 matches in 72 hours to raise money for a local food bank.
On March 19, 2010, O'Reilly competed in a three-way match for the NWA Canadian Heavyweight Championship against champion Billy Suede and Sylum. In April, O'Reilly defeated Rick Sterling at Title vs. Title. He entered the Pacific Cup tournament again on June 6, defeating Azeem and Suede en route to the final where he lost to Artemis Spencer. At To Hell and Back on June 25, O'Reilly wrestled twice in one night, defeating Ice before losing to Sylum in a match for the NWA Canadian Heavyweight Championship. The following night, O'Reilly teamed with El Phantasmo to face Pop Culture in a two out of three falls match, which Pop Culture won, two falls to one. On July 10, O'Reilly lost to Tony Baroni. O'Reilly returned to ECCW to compete in the Pacific Cup tournaments in 2011 and 2014.
O'Reilly returned to ECCW on January 14th 2017 for Ballroom Brawl 7 where he defeated El Phantasmo for the ECCW Championship.
O'Reilly made his Full Impact Pro (FIP) debut at the In Full Force show on May 30, 2008, where he lost to Damien Wayne. He appeared again for FIP the following night at Southern Justice 2008 wrestling Johnny DeBall. The match ended in a no contest when Davey Richards attacked both competitors. He returned to FIP in November 2009, appearing at the Jeff Peterson Memorial Cup, Night 1 where he teamed with Tony Kozina in a Tag Team Rumble which was won by Bumz R' Us.
On January 16, 2010, O'Reilly appeared at the Evolve promotion's inaugural show, where he defeated Bobby Fish. At Evolve 2: Hero vs. Hidaka, O'Reilly defeated Hallowicked, who a replacement for an injured TJP. O'Reilly suffered his first loss in the promotion at Evolve 3: Rise or Fall, when he lost to TJP. He lost his second match to Ricochet at Evolve 5: Danielson vs. Sawa, giving him a record of two wins and two losses.
O'Reilly appeared at Dragon Gate USA (DGUSA)'s Open the Freedom Gate pay-per-view taping on November 28, 2009 on the pre-show, where he defeated Adam Cole. At the DGUSA Fearless pay-per-view, O'Reilly won a six-way match on the pre-show, before he accompanied Davey Richards to the ring for his match. On September 26, 2010, O'Reilly participated in six pack challenge, which was won by Brodie Lee at a DGUSA in Milwaukee.
On August 28, 2010, O'Reilly competed in Chikara's Young Lions Cup tournament, but lost to Adam Cole in the quarter-finals.
O'Reilly made his Ring of Honor (ROH) debut in 2009. On November 13, 2009, Tony Kozina defeated O'Reilly. On the December 21, 2009 episode of Ring of Honor Wrestling, taped on November 5, O'Reilly lost to Chris Hero. At the February 5, 2010 tapings on Ring of Honor Wrestling, O'Reilly defeated Tony Kozina. On April 23, 2010, in Dayton, Ohio, O'Reilly defeated Sampson. On September 10, 2010, O'Reilly was defeated by former ROH World Champion Austin Aries. Three days later, ROH announced they had signed O'Reilly to a contract with the company.
O'Reilly then began to ally himself with fellow ROH newcomer Adam Cole, with the pair forming a tag team. At the October 2 Ring of Honor Wrestling tapings they defeated the team of Grizzly Redwood and Mike Sydal. They lost to Steve Corino and Kevin Steen on October 15, and the All Night Express of Kenny King and Rhett Titus at a show on October 16. They defeated the Bravado Brothers (Lance and Harlem) on the November 8 episode of Ring of Honor Wrestling. On November 12, O'Reilly participated in the 2010 edition of the Survival of the Fittest tournament, but was eliminated by Kevin Steen in the first round. The following night in Toronto, O'Reilly and Cole defeated the Bravado Brothers. O'Reilly made his ROH pay-per-view debut on December 18 at Final Battle 2010, where he and Cole were defeated by the All Night Express (Rhett Titus and Kenny King). On April 1 and 2 at Chapter One and Two of Honor Takes Center Stage, O'Reilly and Cole faced The Briscoe Brothers (Jay and Mark) and The Kings of Wrestling (Chris Hero and Claudio Castagnoli) in two losing efforts, despite putting on strong performances. On July 8, O'Reilly and Cole defeated the Bravado Brothers to earn a future shot at the ROH World Tag Team Championship. On July 25, ROH announced that O'Reilly had re-signed with the promotion. At the August 13 tapings of Ring of Honor Wrestling, the tag team of O'Reilly and Cole was named Future Shock.
At the January 7, 2012, tapings of Ring of Honor Wrestling, Future Shock disbanded and O'Reilly formed a new tag team named Team Ambition with Davey Richards, opposite Adam Cole and Eddie Edwards. Outside of ROH, the team also came to include Tony Kozina. On March 4 at the 10th Anniversary Show, Team Ambition was defeated in a main event tag team match by Cole and Edwards. On March 31 at Showdown in the Sun, O'Reilly faced Cole and defeated him using an underhanded tactic. On June 24 at Best in the World 2012: Hostage Crisis, O'Reilly was defeated by Cole in a "Hybrid Rules" match. Afterward, O'Reilly slapped Cole as he tried to make peace with his former partner and later announced that he was now going after Richards, cementing his heel turn.
On December 16 at Final Battle 2012: Doomsday, O'Reilly and Bobby Fish (known as reDRagon) faced the reformed American Wolves (Davey Richards and Eddie Edwards) in a losing effort. At the following iPPV, 11th Anniversary Show on March 2, 2013, O'Reilly and Fish defeated the Briscoe Brothers for the ROH World Tag Team Championship. The same month, they successfully defended the championship against Alabama Attitude (Corey Hollis and Mike Posey), before retaining it at Best in the World 2013 in June in a three-way match against the C & C Wrestle Factory (Caprice Coleman and Cedric Alexander) and S.C.U.M. (Cliff Compton and Rhett Titus). They lost the title to the Forever Hooligans (Alex Koslov and Rocky Romero) on July 27, but regained the title from the American Wolves on August 17. Over the next several months reDRagon successfully defended the championship against teams including the C & C Wrestle Factory, the Forever Hooligans, and Jay Lethal and Michael Elgin. They retained the championship against Outlaw, Inc. (Homicide and Eddie Kingston) at Final Battle 2013 in December and Adrenaline Rush (ACH and TaDarius Thomas) at the 12th Anniversary Show in February 2014. On March 8, 2014, reDRagon lost the title to The Young Bucks. ReDRagon regained the tag team championship from The Young Bucks on May 17, at the ROH and New Japan Pro Wrestling (NJPW) co-promoted pay-per-view War of the Worlds. They successfully defended the championship against The Briscoe Brothers on June 7 and against Christopher Daniels and Frankie Kazarian at ROH's first live pay-per-view Best in the World 2014 on June 22. On November 23, reDRagon defeated ACH and Matt Sydal, The Addiction (Daniels and Kazarian), and The Briscoes to retain the ROH World Tag Team Championship and win the Tag Wars tournament. They followed up their victory with successful title defenses against the Time Splitters (Alex Shelley and Kushida) at Final Battle 2014, The Young Bucks in March 2015 at ROH's 13th Anniversary Show, and The Kingdom (Michael Bennett and Matt Taven) at Supercard of Honor IX. O'Reilly and Fish lost the tag team title to The Addiction at the Ring of Honor Wrestling tapings on April 4. On September 18, 2015, at All Star Extravaganza VII, O'Reilly received a shot at the ROH World Championship, but was defeated when Adam Cole turned on him.
On August 19, 2016, at Death Before Dishonor XIV, O'Reilly made his return and surprisingly interrupting Cole's victory celebration as the two-time ROH World Champion by attacking him, thus reigniting their feud. On December 2 at Final Battle, O'Reilly defeated Cole to win the ROH World Championship for the first time. On December 31, O'Reilly's ROH contract expired. He was said to be reviewing his future options and working for ROH on a per date agreement until he made a decision. On January 4, 2017, O'Reilly lost the ROH World Championship back to Cole at NJPW's Wrestle Kingdom 11 in Tokyo Dome. On January 11, 2017, O'Reilly was removed from the ROH roster page and pulled from all upcoming ROH events, indicating his contract with Ring of Honor had expired, ending his 8-year tenure with the company.
On October 22, 2011, O'Reilly debuted in Pro Wrestling Guerrilla alongside regular tag team partner Adam Cole as Future Shock. They unsuccessfully challenged The Young Bucks (Matt and Nick Jackson) for the PWG World Tag Team Championship. At Fear on December 10, Future Shock were defeated by the RockNES Monsters (Johnny Goodtime and Johnny Yuma). On April 21, 2012, Future Shock entered the annual Dynamite Duumvirate Tag Team Title Tournament (DDT4), where they made it to the semifinals, before losing to the eventual tournament winners, the Super Smash Bros. (Player Uno and Stupefied). On July 21 at PWG's ninth anniversary event, Future Shock unsuccessfully challenged the Super Smash Bros. for the PWG World Tag Team Championship in a three-way ladder match, which also included The Young Bucks. On January 12, 2013, Future Shock entered the 2013 Dynamite Duumvirate Tag Team Title Tournament. After defeating the DojoBros (Eddie Edwards and Roderick Strong) in their first round match, the team was eliminated from the tournament in the semifinals by El Generico and Kevin Steen.
On August 30, O'Reilly entered the 2013 Battle of Los Angeles, defeating Trent? in his first round match. The following day, O'Reilly first defeated ACH in the second round, then Drake Younger in the semifinals and finally Michael Elgin in the finals to win the 2013 Battle of Los Angeles and become the number one contender to the PWG World Championship, held by his former Future Shock partner Adam Cole. O'Reilly received his title shot on October 19, but was defeated by Cole, following interference from Kevin Steen and The Young Bucks. O'Reilly received a rematch for the PWG World Championship in a "Knockout or Submission Only" match on May 23, 2014, and defeated Cole to become the new champion. In August, O'Reilly made it to the semifinals of the 2014 Battle of Los Angeles, but was forced to withdraw from the match after suffering a storyline injury at the hands of Roderick Strong. On December 12, O'Reilly successfully defended the PWG World Championship against the 2014 Battle of Los Angeles winner Ricochet, only to lose it to Strong in an impromptu Guerrilla Warfare match immediately afterward.
Through ROH's relationship with NJPW, reDRagon made an appearance for the Japanese promotion on August 10, unsuccessfully challenging Time Splitters (Alex Shelley and Kushida) for the IWGP Junior Heavyweight Tag Team Championship. reDRagon returned to NJPW on October 25 to take part in the 2014 Super Jr. Tag Tournament. On November 3, reDRagon defeated The Young Bucks in the finals to win the tournament. Five days later at Power Struggle, reDRagon defeated Time Splitters in a rematch to become the new IWGP Junior Heavyweight Tag Team Champions. They made their first successful title defense on January 4, 2015, at Wrestle Kingdom 9 in Tokyo Dome, in a four-way match against Forever Hooligans, Time Splitters and The Young Bucks. On February 11 at The New Beginning in Osaka, reDRagon lost the title to The Young Bucks in a three-way match, also involving Time Splitters. reDRagon returned to NJPW on May 3 at Wrestling Dontaku 2015, where they unsuccessfully challenged for the IWGP Junior Heavyweight Tag Team Championship in a three-way match with Roppongi Vice (Beretta and Rocky Romero) and The Young Bucks. Later that month, O'Reilly entered the 2015 Best of the Super Juniors. Finishing with a record of six wins and one loss, he won his block and advanced to the finals of the tournament. On June 7, O'Reilly was defeated in the finals of the tournament by Kushida. Following the tournament, reDRagon received a rematch for the IWGP Junior Heavyweight Tag Team Championship in a three-way match, also involving Roppongi Vice, but were again defeated by The Young Bucks on July 5 at Dominion 7.5 in Osaka-jo Hall. On August 16, reDRagon defeated The Young Bucks to win the IWGP Junior Heavyweight Tag Team Championship for the second time. They lost the title back to The Young Bucks in a four-way match that also included Roppongi Vice and Matt Sydal and Ricochet on January 4, 2016, at Wrestle Kingdom 10 in Tokyo Dome. On October 10 at King of Pro-Wrestling, O'Reilly received his first singles title shot in NJPW, when he unsuccessfully challenged Katsuyori Shibata for the NEVER Openweight Championship.
Greenwood has type 1 diabetes. He cites Bret Hart, Toshiaki Kawada, Royce Gracie, and Muhammad Ali as his role models. Growing up, Greenwood participated in several sports, including amateur wrestling, ice hockey, football, lacrosse, kickboxing, Jiu-jitsu, and snowboarding, and briefly played rugby in Europe. He remains part of a rugby club. While training to become a professional wrestler, he worked as a cook at a local restaurant. Greenwood once lived with Davey Richards and Tony Kozina.Finishing moves
ARMageddon (Cross armbreaker)
Ax and Smash (Scissors stomp to a kneeling or bent-over opponent's head followed by an elbow smash)
Bridging leg hook belly-to-back suplex
Nigel (Pendulum lariat) – adopted from Nigel McGuinness
Front missile dropkick from the ring apron to the outside of the ring
Triple rolling double underhook suplex
"The Martial Artist"
"I'm Shipping Up to Boston" by Dropkick Murphys
"Dance Away" by Damn Valentines
Elite Canadian Championship Wrestling / NWA: Extreme Canadian Championship Wrestling
ECCW Championship (1 time)
NWA Canadian Junior Heavyweight Championship (3 times)
Pacific Cup (2007)
High Risk Wrestling
HRW Tag Team Championship (1 time) – with Bobby Fish
New Japan Pro Wrestling
IWGP Junior Heavyweight Tag Team Championship (2 times) – with Bobby Fish
Super Jr. Tag Tournament (2014) – with Bobby Fish
Pro Wrestling Guerrilla
PWG World Championship (1 time)
Battle of Los Angeles (2013)
Pro Wrestling Illustrated
PWI ranked him 32 of the top 500 singles wrestlers in the PWI 500 in 2016
Pro Wrestling Prestige
PWP Tag Team Championship (1 time) – with Davey Richards
Ring of Honor
ROH World Championship (1 time)
ROH World Tag Team Championship (3 times) – with Bobby Fish
ROH World Tag Team Championship #1 Contender Lottery Tournament (2011) – with Adam Cole
Tag Wars Tournament (2014) – with Bobby Fish
Match of the Year (2012) with Adam Cole vs. Super Smash Bros. (Player Uno and Stupefied) and The Young Bucks on July 21
St. Louis Anarchy
Medallion Tournament (2012)