Top 14 Old School Conor McGregor Fights

Conor McGregor was catapulted to fame and fortune when he signed for the UFC in 2013, but this was far from an overnight success story, as he’d spent years learning his craft on the regional circuit before earning his big break.

At the age of 19, McGregor dared to be different, walking away from a steady job as a plumber to pursue his dream of becoming a mixed martial arts star, informing his shocked parents that he’d be a millionaire by the time he was 25.

It seemed like a one-in-a-million shot, but though it took him a year longer than he’d anticipated, ‘The Notorious’ did indeed become a millionaire – multiple times over in fact – while becoming not only the UFC’s featherweight champion, but also the biggest star in the sport.

In this article we’ll offer you a chance to go right back to the beginning of this modern day rags-to-riches story and witness history being made, from his pro-debut in his own hometown back in 2008, right the way through to his final fight in the Cage Warriors promotion at the end of 2012 that would lead to him signing for the UFC.

Conor McGregor Vs Gary Morris

In March of 2008, at just 19 years of age, a youthful, clean-shaven Conor McGregor made his professional MMA debut in his home city of Dublin, Ireland for ‘Cage Of Truth’, a local promotion ran by his coach, John Kavanagh.

Competing at lightweight, McGregor was to face fellow newcomer Gary ‘The Dumptruck’ Morris, another local fighter who came from a Judo background.

McGregor’s amateur boxing background gave him an edge over Morris in the striking department and led to him dropping Morris with a straight left early in the second round, then finishing him off with ground and pound for the TKO victory.

Conor McGregor Vs Mo Taylor

McGregor’s impressive debut caught the attention of the leading UK promotion at the time, Cage Rage, who recruited McGregor for the next instalment of their ‘Contenders’ series in Dublin just a few months later in May of 2008.

McGregor was paired up against another young fighter, Mo Taylor, who was making his pro debut that night.

McGregor’s youthful exuberance was on display here as he teed off with a combination of punches against the cage just seconds into the fight and then unleashed three kicks in a row as Taylor tried to back out of danger.

It wasn’t long before McGregor again had Taylor backed up against the cage, drilling him with repeated left and right hands until he crumpled to the mat.

McGregor had to fight off an armbar attempt as he worked ground and pound on the mat, and then continued chipping away until the ref ended the contest by TKO with just 66 seconds on the clock.

Conor McGregor Vs Artemij Sitenkov

Looking to continue the successful start to his MMA career, McGregor returned to the ‘Cage Of Truth’ promotion a couple of months later to take on the more experienced Artemij Sitenkov, a Lithuanian fighter with a 5-4 record at the time.

’The Notorious’ dropped down to featherweight for the first time that night, but the fight didn’t go according to plan, with Sitenkov pulling guard early in the contest and exposing the holes in McGregor’s ground game by catching him in a kneebar submission in just 69 seconds.

Conor McGregor Vs Stephen Bailey

McGregor’s first loss took a toll on him, but he returned to action in Dublin at ‘KO: The Fight Before Christmas’ in December of 2008.

Going up against the similarly unseasoned Stephen Bailey in a featherweight bout, McGregor made his impression felt quickly by dropping him with a left hook.

McGregor then smoothly moved into full mount and starting unloading ground and pound strikes to rack up another quick TKO win with 1.22mins on the clock, and end the year on a high.

Even at this early stage in his career, McGregor’s confident swagger was in full effect as he wandered over to a near-by camera and simply declared, “I’m the f*ckin’ future.”

Conor McGregor Vs Connor Dillon

Despite the early promise that he’d shown, McGregor’s future in fighting looked to be hanging in the balance as he started falling in with the wrong crowd and stopped showing up at the gym.

McGregor’s mother became concerned with the direction his life was heading and pleaded with his coach, John Kavanagh to help steer him back on course, and that’s just what he did.

It’d be almost two years since his last fight when McGregor finally got back to business against Connor Dillon at Chaos FC 7 in October of 2010.

Dillon was also an up and coming prospect at the time, with a 2-1 record, but McGregor was not impressed and was showboating from the opening bell, constantly taunting his opponent.

The fight ended in unfortunate fashion late in the first round though as Dillon’s foot was left badly injured after clashing with McGregor’s knee, leaving him unable to continue.

It wasn’t ideal circumstances, but a win is a win, and McGregor was happy to take it.

Conor McGregor Vs Joe Duffy

Two months later McGregor was handed a big opportunity to fight Joe Duffy at respected UK promotion Cage Warriors 39th event in Cork, Ireland.

This was undoubtedly the toughest test of McGregor’s career so far, going up against another highly touted Irish prospect, who had already amassed an impressive 7-0 record at the time.

McGregor had been working hard on his ground game heading into this fight, but it wouldn’t prove to be enough against the well-rounded Duffy.

’The Notorious’ started the fight brightly enough, landing some clean shots and quickly opened up a cut above ‘Irish Joe’s’ left eye.

However, Duffy deftly switched gears, landing a nice takedown and moments later forced McGregor to tap by way of an arm triangle choke.

The whole fight had lasted just 38 seconds, and left McGregor with an overall 4-2 record in the sport.

Conor McGregor Vs Hugh Brady

A few months after his loss to Joe Duffy, McGregor looked to get back on the saddle against Hugh Brady at Chaos FC 8 in February of 2011.

Brady had respectable 4-1 record heading into this fight and a few submission victories on his record, along with a KO win in his previous outing.

After a brief feeling out process in the first couple of minutes of the fight, McGregor put Brady back on his heels with a powerful straight left.

However, it was a vicious uppercut soon afterwards that sent his opponent crashing to the canvas, with ground and pound sealing the technical knockout victory 2.31mins into the fight.

Conor McGregor Vs Mike Wood

McGregor wasted no time in getting back into the cage, with his next fight coming just a month later against Mike Wood at ‘Cage Contender 8’ in Dublin.

Wood had a 1-1 record at the time and was taking the fight on just two days notice, and he’d prove to be no match for ‘The Notorious’.

A piston-like left hand mere seconds into the fight rocked Wood, and a left hook followed that put him on his knees.

Wood tried to get back up, but was greeted by three left hooks that delivered the KO stoppage.

From start to finish the fight had lasted just 16 seconds, but Wood left the cage with a broken orbital bone.

Conor McGregor Vs Paddy Doherty

McGregor was on a roll now and took his third fight in three months against Paddy Doherty at ‘Immortal Fighting Championship 4’ in April of 2011.

If you thought his last fight was quick, then this one really was a ‘blink and you’ll miss it’ affair against Doherty, who had compiled a 4-6 record.

Just four seconds into the fight McGregor unloaded with a powerful left hook that sent the incoming Doherty thumping to the mat, and that was that – McGregor extended his winning streak to three fights by notching his second KO victory in a row.

Conor McGregor Vs Artur Sowinski

With his confidence running high, McGregor sought to maintain his momentum with a headlining fight at ‘Celtic Gladiator 2’ opposite Poland’s Artur Sowinski.

Sowinski, who these days is KSW’s featherweight champion, was McGregor’s most experienced opponent at the time, wielding an 11-4 record – a definite step up in competition.

Fighting in a tiny cage in front of a raucous crowd, Sowinski tested McGregor’s still developing ground game in the opening minute of the fight by taking him down and threatening with a guillotine choke.

The Irishman stayed calm though and was able to escape and get back upright, where he continued to show his developing all-round game by mixing up his crisp boxing with takedowns and work in his opponent’s guard.

By the end of the round Sowinski was flopping onto his back just to get some respite from McGregor’s razor-sharp offensive output and was sporting a nasty looking mouse under his right eye.

For the first time since his debut, McGregor headed into the second round, where he’d quickly drop Sowinkski with a hard left hook that would have knocked out lesser men, then finished him off with ground and pound from full mount for the TKO.

Conor McGregor Vs Aaron Jahnsen

With four victories in a row under his belt, an 8-2 overall record and never having gone past the second round, McGregor’s reputation was growing rapidly, and that re-ignited the interest of the Cage Warriors promotion, who signed him up to a five fight deal.

McGregor was lined up to fight another future UFC fighter Nicklas Backstrom at Cage Warriors: Fight Night 2 in September of 2011, but when he pulled out, Norwegian up and comer Aaron ‘Iron Fist’ Jahnsen stepped in on very late notice instead.

This would mark the first time that ‘The Notorious’ would be fighting outside his native Ireland, with the even taking place in Amman, Jordan of all places.

The exotic location and late shift in opponent didn’t phase McGregor however, as he was able to partially knock Jahnsen down with a left hook mid-way through the opening round, got on top and started punishing him with ground and pound that left the Norwegian covering up until the referee finally stepped in to wave the fight off.

Conor McGregor Vs Steve O’Keefe

McGregor had racked up a total of five victories during a busy 2011, and he aimed to build on that with his first fight in 2012 against Steve O’Keefe at Cage Warriors 45 in England.

McGregor experienced a tough weight cut to 145lbs for the match-up against the equally in-form O’Keefe, who was on a six fight winning streak at the time.

It looked to be a tough match-up on paper, but McGregor took the fight to O’Keefe from the opening bell, unleashing a three-piece combo and then following up with hard knees from the muay thai clinch.

McGregor then showed off his ever-improving takedown defense as he thwarted O’Keefe’s attempts to get to the mat, and made him pay for a failed single leg takedown against the cage by raining down hard elbows to the head that KO’d the Englishman.

Conor McGregor vs Dave Hill

In a short space of time McGregor had made a name for himself in the Cage Warriors promotion, and his overall six fight winning streak earned him a shot at the vacant featherweight title shot next time out against Dave Hill.

With a 10-2 record, Hill was a worthy challenger, but Hill admitted to the 42.ie website several years later that McGregor’s cocky attitude, seemingly unflappable self-belief and pre-fight trash-talk took him by surprise and, “threw me off more than I’d like to admit.”

This would prove to be McGregor’s most accomplished performance so far, shrugging off Hill’s takedown attempts, but still showing a willingness to go to the mat, and indeed he spent large portions of both the first and second rounds on top.

His striking was as dangerous as ever, and again there was real development here too as kicks started to play a more significant role in his offensive output, dropping his opponent in both rounds as a result.

The icing on the cake was the fact that he managed to submit Hill with a rear-naked choke late in the second round, the first submission of his career, to become the new Cage Warriors featherweight champion.

McGregor celebrated the win in style, vaulting the cage and running into the overjoyed Dublin crowd.

Conor McGregor Vs Ivan Buchinger

Already a hero in his native Ireland, McGregor was brimming with potential star power, and Cage Warriors embraced the moment, allowing ‘The Notorious’ to move up to fight for their vacant lightweight title at the end of the year.

This time McGregor would be going up against the battle-hardened Slovakian fighter Ivan Buchinger, who boasted an impressive record of 21-3, compared to the Irishman’s 11-2 run.

Now sporting his trademark beard and appearing even more self-assured, McGregor looked better than ever against Buchinger, including adding new eye-catching spinning kicks to his resume.

It was his quick, accurate hands and devastating power that had the biggest impact though, with his straight left tagging his opponent at will, before a thundering left hook sent Buchinger toppling in slow motion to the canvas for the first round knockout finish.

Adding another highlight-reel stoppage to his resume, McGregor was now riding an eight-fight winning streak and had just become a dual-weight champion in the Cage Warriors, so it’s little wonder that the UFC then rolled out the red carpet for this future superstar, and the rest is history.