Orange Cassidy’s 15 Best Matches In AEW History

AEW has shone the spotlight on a number of talents who, for one reason or another. Some of them have proven to be huge stars. One of them is Orange Cassidy, and in this article we will look at Orange Cassidy’s best matches in AEW.

He made his AEW debut at the first ever AEW pay-per-view, Double or Nothing 2019.

Cassidy appeared as part of the Casino Battle Royale, entering late (as he was too lazy to come in on time). He immediately locked horns with Tommy Dreamer, and it was the first time many fans watched as he performed his trademark “lazy” kicks.

Since then, he has gone from strength to strength. Cassidy joined forces with Best Friends Chuck Taylor and Trent, before adding Kris Statlander and Wheeler Yuta to their team.

He has challenged for the TNT championship multiple times, as well as the AEW World Championship.

He fell short in those instances, but the door is not shut for Cassidy yet. I’m sure we will see Orange Cassidy as AEW Champion at some point in the future.

He has since won the AEW All-Atlantic Championship (now named the AEW International Championship) and is one of the most impressive in AEW.

Orange Cassidy puts on the best matches each night, with the crowd in the palm of his hand each time.

Along the way, he has quietly had some of the best matches in AEW. Despite being viewed as merely a “comedy gimmick” early on in his run, he has shown AEW fans everywhere that he is one of the best wrestlers in the company.

There is a reason so many top stars like Chris Jericho and Kenny Omega have worked with Freshly Squeezed. He is a top talent and an absolute main event star for AEW.

Here are the top 10 list of Orange Cassidy’s best matches, ranked in order from worst to best.

Orange Cassidy’s Best Matches

Here is a list of 15 of Orange Cassidy’s best matches in AEW. We’ll go through each match, giving our thoughts and explaining why these are some of the greatest in his career.

Let us know what your favourite Orange Cassidy matches are, down in the comments section below.

15. Blackjack Battle Royale – Double or Nothing 2023

Opening AEW Double or Nothing 2023, Orange Cassidy won one of the best battle royales in AEW history.

He defended his AEW International Championship for the 24th time, against 20 of the top challengers in the division.

Cassidy fought off the likes of Jay White, Big Bill and Keith Lee to retain his gold, surviving despite a slew of injuries.

He last eliminated Swerve Strickland, lazily kicking him off the apron after feigning a punch, keeping his belt for at leat one more week in one of his best matches so far.

14. vs United Empire – AEW Dynamite June 22nd, 2022

Despite the incredible derision by Jim Ross on commentary, the match between CHAOS and United Empire on AEW was a fantastic bout.

They did flout the tag rules at times (although that’s par for the course in AEW), as the trio of Orange Cassidy, Trent and Rocky Romero took on Aussie Open and Will Ospreay, in a dream match of sorts.

The match felt like a PWG-stlye match, and was a fun spot fest that had the crowd on its feet from the first minute. A wild Dynamite opener that helped build the story between Ospreay and Cassidy, leading up to their bout in Forbidden Door (more on that later).

13. vs Katsuyori Shibata – AEW Rampage, November 4th, 2022

In his second real match back in wrestling since an enforced retirement, Katsuori Shibata looked back in form against Orange Cassidy.

Battling for the All-Atlantic title, Cassidy was trusted to keep Shibata safe, and protect his head, after he nearly died in his match with Okada years prior in New Japan.

He did just that, as well as pulling out one of the best matches of the legendary title reign.

Cassidy won the bout with an Orange Punch, and gave fans hope that we’d see the old Shibata back one day, ready to get his revenge against Kazuchika Okada.

12. vs PAC – AEW Dynamite, October 12th, 2022

In the first bout between these two on this list, Orange Cassidy vs PAC remains one of the best rivalries in AEW history.

Orange Cassidy beat PAC to win the AEW All-Atlantic Championship. This was his crowning moment in AEW, being the first belt he won in the company, despite challenging for every other men’s belt in the AEW.

He was immediately pushed as a fighting champion, being given weekly title defences against a wide variety of challengers.

This match was a spot-filled, fast-paced match, that was very different to their other encounters, but a great addition to their respective canons.

11. vs Cody Rhodes – AEW Dynamite, October 14, 2020

Cody Rhodes vs Orange Cassidy is one of the best matches of either man’s AEW run.

This match came just 2 weeks after Cassidy lost a title match to then-champion Mr Brodie Lee. Cody would defeat Brodie Lee the week after, in what would turn out to be the former Intercontinental Champions final ever match.

Cody Rhodes defended his title on AEW Dynamite against the top ranked Orange Cassidy. It started out as a typical Orange Cassidy match, which happen to be my favourite.

Cassidy, not really caring about the match, lazily dodged any attempt to wrestler from Cody, before a push from Cody knocks his glasses off.

This angered Orange Cassidy, who outwrestled Cody and almost won the match with a number of creative pinfall attempts.

The match was beautifully paced, with Cody almost playing the heel to the ultimate underdog babyface that is Orange Cassidy. The Dark Order tried to interfere, attempting to hit Cody with his TNT title. However, Orange Cassidy took the championship from him, wanting to fight Cody in a fair fight.

Cassidy’s selling was a joy to watch in this match, showing why he is one of the best wrestlers in all of AEW.

The matches ending was one of the best executed in AEW history. Orange Cassidy hit a beach break on Cody on the apron, rolling him inside and going for the pin. However, Cody tries to roll him up, and the pair trade moves.

Cassidy hits the beach break again, but Cody kicks out of the pinfall. Orange goes for the Orange Punch but trips, allowing Cody an in. However, Cassidy attempts one of his creative pins, with only seconds remaining on the clock.

He has Cody beaten, but before the ref can slap the mat for the third time, the bell rings to signify that time has run it. The match is a time limit draw and Cody retains the belt.

The match had me on the edge of my seat the whole way through, and especially the last five minutes. Orange Cassidy played the underdog babyface to perfection, and brought out one his and Cody Rhodes best matches in AEW.

10. vs Mr Brodie Lee – AEW Dynamite – September 23rd, 2020.

Just weeks before he would wrestle his final match against Cody Rhodes, Brodie Lee defended his TNT Championship against the number one contender, Orange Cassidy.

Formerly Luke Harper in WWE, Brodie Lee passed away on Boxing 2020 after a battle with illness which was kept a secret from fans of the wrestler.

The match showcased the incredible size and strength of the Dark Order leader. He threw Cassidy around like a rag doll, and was helped by repeated interference from the likes of John Silver and Evil Uno.

The whole match is spent for you waiting for Orange Cassidy to pull through and steal the win from Brodie, and win the title.

However, at the end of the match, Cassidy starts to make a comeback, but is hit by a huge powerbomb and viscous discuss clothesline. He’s pinned for the loss, and Brodie Lee retains his title.

It’s a fun match to watch, especially if you want to see Brodie Lee is AEW. His career in AEW was short, and the thought of what could gave been.

If you want to read more about Brodie Lee, check out our article on Brodie Lee’s best matches.

9. vs Miro – AEW Dynamite, November 3rd, 2021

Due to Jon Moxley seeking help for his battle with alcohol, he was not available to face Orange Cassidy.

The pair were due to do battle in the semi-final of the AEW World Championship number one contender eliminator tournament, with the winner facing Bryan Danielson at Full Gear.

Luckily, AEW managed to substitute in one of their biggest stars and best character to take Moxley’s place.

God’s Favourite Champion, the former TNT Champion Miro stepped up to take his place, and take on Orange Cassidy in AEW Dynamite’s main event match.

Despite losing his TNT title some weeks ago, Miro was on a mission to destroy Orange Cassidy here.

He brutalised the smaller wrestler, throwing him around the ring with ease. He executed chains of suplexes which were sold beautifully by Cassidy.

Miro looked like a monster, and Cassidy once again proved why he is the best underdog in wrestling right now.

Cassidy took any openings he saw in the match, hitting Miro with a stunner and an elbow drop from the top rope, through a table on the outside.

But Miro was relentless. The beating became too much for Cassidy.

He fought as hard as he could, but eventually Miro locked in the Game Over submission, and Orange Cassidy could do nothing but tap out.

The match itself was a short one. It was less than 10 minute, but showcased exactly what it needed to.

For my money, it was one of Orange Cassidy’s AND Miro’s best matches. It was a simple story, told perfectly and made both wrestlers look like stars.

8. Casino Ladder Match – AEW Double or Nothing 2020

The first ladder match on this list, and the one with some of the best comedy in wrestling I’ve ever seen.

This Casino Ladder match was for a shot at Jon Moxley’s AEW Championship. It was contested between nine different wrestlers.

Joining Orange Cassidy in his seventh best match in AEW were a gluttony of stars. Darby Allin, Colt Cabana, Scorpio Sky, Joey Janela, Kip Sabian, Frankia Kazarian and Luchasaurus all competed in this.

They were joined by the joker card, the new signing to AEW that was Brian Cage. Cage had signed for AEW in January, but an injury kept him out of action until double or nothing.

The match was a brilliant one, and one you definitely should go an watch. The real highlight though was Orange Cassidy’s involvement.

When he made his entrance, he went over to the announce table, and asked Excalibur what the rules of the match were.

He then, when told he had to climb the ladder and retrieve the poker chip, looked visibly annoyed and slowly walked toward the ring.

When in the ring, he simply tried to reach up and grab the chip. It did not work.

Then he grabbed a ladder, but as he was too lazy, he simply lay it on it’s side rather than erected it. He then stepped up on the ladder, and obviously still could not reach the top.

The match was won by Brian Cage, but featured some fearsome bumps and incredible aerial assaults.

7. vs Rey Fenix – AEW Dynamite, May 20th, 2020

This match came very early on in the pandemic era. It could very well have been higher on this list, but the lack of crowd really hurt this match. With how rabid the crowds are for Rey Fenix and Orange Cassidy, they could have turned an excellent match into one of each man’s best matches.

The match was short, and used to build up to the Casino Ladder match at AEW Double or Nothing 2020. Rey Fenix and Orange Cassidy were set to both be in that match, but unfortunately Fenix would be forced to pull out of the event due to injury.

However, he was fit and raring to go for his match against Orange Cassidy. It wasn’t like a usual Rey Fenix match, though.

Fenix wasn’t his usual balls to the wall, high flying self. He worked as the heel in the match, beating down Orange Cassidy with brutal kicks and disgusting chops.

Cassidy played the victim for the bulk of the match. He took some harsh bumps from Fenix, including a baseball slide from Fenix which launched him into the camera, smashing his head on the camera.

The matches ending takes away from it slightly. Kip Sabian, another entrant in the ladder match, interrupted the match carrying a ladder. He set it up outside the ring, and sat at the top watching the match unfold.

Cassidy got distracted, which allowed Fenix to hit a rolling cutter and pinning him for the victory.

While this was one of Orange Cassidy’s best matches, the distraction ending by Kip Sabian took away from the match. Really, I’d want to see more between these two, giving them more time and letting him do more of his high-flying move set.

6. vs Chris Jericho – AEW Fyter Fest 2020

Out of the trilogy of battles between Chris Jericho and Orange Cassidy, their Fyter Fest match is certainly the best.

The result was not the best, especially as it was Cassidy’s first taste in a main event spotlight.

However, the in ring action was top notch. Cassidy played the hero to Jericho’s villain, and solidified himself as someone who can work with main event talent like Jericho.

Orange Cassidy should have won this match, as he did two of the three times they faced off.

However, one of those was in the Mimosa Mayhem match, which while entertaining was definitely the weakest of the three bouts.

5. Casino Ladder Match – AEW Dynamite, October 6th 2021

The second Casino ladder match on this list, and the most recent featuring Orange Cassidy. It ranks in at number four for the list of the best Orange Cassidy matches.

After Kenny Omega defeated Christian Cage at All Out, and drew with Bryan Danielson on Dynamite, the AEW Championship was lacking a top contender.

Thus, a seven man ladder match was set to find out who would face him at AEW Full Gear 2021.

Orange Cassidy was announced as one of the participants of the match.

He was joined by six other men, including Matt Hardy, who he had been feuding with for months. Other wrestlers in the match were PAC, Andrade, Lance Archer and Jon Moxley, as well as the surprise “Joker Card“.

The match was as brutal as you’d expect from a multi-man ladder.

Suplexes onto ladders, jumping off ladders, throwing ladders at each other. All sorts of ladder-based violence was on the menu for this match.

Cassidy suffered one of the worst bumps on the show. He brawled with Jon Moxley for a while, before moving on to fight with Matt Hardy.

Hardy beat up Freshly Squeezed, laying him out on top of a ladder on the outside. Hardy then climbed another ladder, and leg dropped Cassidy through the ladder, breaking it in half.

The match would be won by the joker card of the match, which turned out to be Hangman Adam Page.

His debut was a great return for the Hangman, and the match ranks up there with one of Orange Cassidy’s best.

4. Orange Cassidy & Chuck Taylor vs Miro & Kip Sabian – Arcade Anarchy

With Trent out with a bad injury, it came down to Orange Cassidy to team up with his Best Friends teammate for this bout.

The Best Friends had been in a feud with Miro and Kip Sabian since Miro’s AEW debut. They had battled in multiple matches, with Chuck Taylor even becoming Miro’s butler at one point. It was a silly but fun storyline which helped introduce Miro to the AEW fans.

The feud culminated in a unique match up for the two teams. They faced off in an Arcade Anarchy match.

This match came about because the Best Friends accidentally destroyed Miro’s arcade machine. His gimmick was being a gamer for some reason, we don’t talk about it anymore. Just move on.

They went on to ruin Kip Sabian and Penelope Ford’s wedding at AEW Beach Break, setting up the grudge match between the two teams.

The match featured no disqualification rules, and had arcade machine and various carnival games surrounding the ring.

It was a hard hitting bout, which featured some fun moments and two surprise returns. First, Kris Statlander returned, popping up from inside a grabber machine to attack Penelope Ford.

The other was Trent, returning from injury to help the Best Friends achieve victory. It was a fantastic match, and the Best Friends best match, apart from the Best Friends vs Santana and Ortiz bout.

3. Kenny Omega vs PAC vs Orange Cassidy – AEW Double or Nothing 2021

Orange Cassidy has so far only received one chance at the AEW Championship. It could be a while until we see AEW Champion Orange Cassidy.

However, when he did face off against Kenny Omega and PAC at AEW Double or Nothing 2021, it produced one of the best matches of his career.

The match was the main event of the pay per view, and really emphasised Orange Cassidy’s ability to be a main event player in AEW. It went 1000 miles an hour, and all three men pulled out all the stops to pull out one of the best AEW matches ever.

At multiple points, AEW had you believing that Orange Cassidy was going to become the AEW World Champion. The match had a big fight feel, and really felt like the culmination of Omega’s run as champion.

Cassidy almost got pinned by PAC after being hit by his Black Arrow finishing move, but Kenny Omega broke up the pin at the very last second.

Later on, Cassidy almost became the AEW Champion. He hit Omega with his Orange Punch finisher, but Omega rolled up Freshly Squeezed for the flash pin fall victory. It was a shock ending to a brilliant match.

It came painfully close to being top of the list of Orange Cassidy best matches. However, he had one more bout at AEW Revolution 2020 that just pipped it to the post…

2. vs PAC – AEW Revolution 2020

Nearing the top of the list of the best Orange Cassidy matches in his bout with PAC at AEW Revolution.

Orange Cassidy came out of his shell at AEW Revolution, and showed himself to be a main event calibre wrestler.

PAC vs Orange Cassidy was thrown together, with only a week of build, it was one of the matches of the night on the best pay-per-view in AEW history.

Orange Cassidy faced PAC, in a unique match that showcased Orange Cassidy’s unique wrestling style with the brutality of the Bastard PAC.

PAC came out as the winner, but it was Orange Cassidy who came out looking like the star he is. Without this match with PAC, I don’t think Orange Cassidy would be in such a prominent position in AEW as he is.

The match was the first time in AEW that Cassidy really “tried”. However, he didn’t betray his roots and try too hard. He still did his trademark “wrestling with his hands in his pockets”. It truly is a great match, and one of the best matches in AEW history.

1. vs Will Ospreay – Forbidden Door 2022

The best match of Orange Cassidy’s AEW career was the Forbidden Door clash with NJPW’s Will Ospreay.

At Forbidden Door, in the middle of the card, Will Ospreay wrestled Orange Cassidy. While this was not the most anticipated match on the card, by the end of the show it was named as one of the matches of the year.

The bout showcased both men perfectly. Their characters were clear and they bounced off each other with ease.

Will Ospreay was an arrogant, demeaning wrestler who didn’t think Cassidy was on his level. Cassidy knew he was, but could not be bothered to try at first.

However, once he put his hands in his pockets, then his mastery began and we had a match on their hands.

If you didn’t think Orange Cassidy was great before this match, then you’d be a fool to say otherwise afterwards. He used his gimmick perfectly to antagonise Ospreay, with the clash of styles being the key story behind the match.

The match balanced comedy and serious wrestling, giving a little something for everybody in the crowd to enjoy. Cassidy also showed his incredible “wrestling with his hands in his pockets”, something that nobody else in the world can do.

During the match, Ospreay dominated and never looked like losing. However, the incredible underdog performance by Cassidy gave you glimmers of hope, daring to show you a glimmer of a chance of victory for freshly squeezed.

Will Ospreay won the match in the end, but this match just further proved to the world that Orange Cassidy is one of the best in the world.

What do you think is Orange Cassidy’s best match in AEW? Tell us what you think, down in the comments section below.