In a series new to 2019, we revisit moments in history involving the Sydney Swans’ round-by-round opposition.

History, nostalgia and memories form a special part of what makes Australian rules football great, and we hope the Footy Flashbacks series reignites some of your fondest Swans moments.

In the latest edition, we wind back time to the day Michael O’Loughlin played his 300^th game in a 2009 clash with Richmond.

When Michael O’Loughlin arrived at the Sydney Swans in November 1994 as a skinny and homesick 17-year-old, he thought he’d survive just one year and be “delisted and shipped back to Adelaide”.

But 14 years later – in a 55-point win over Richmond at the MCG in Round 19, 2009 – the boy from Salisbury in Adelaide’s north would become the first Swan in history to play 300 games.

“The club at the time had been around for almost 140 years, and to become the first player to play 300 games – I still pinch myself,” O’Loughlin told Swans Media.

“I had never thought that would be achievable.”

O’Loughlin missed home so much after landing in Sydney that he’d call his mum Muriel twice a day every day.

The Indigenous Swan once even booked his own flight bound for Adelaide and jumped on the phone to let his mum know, only for her to bluntly tell him he’d be sleeping outside.

It was tough love and O’Loughlin says he can’t thank his beloved mum enough.

The banner looking stunning for Michael O'Loughlin's 300th game.

But upon reflection of reaching 300 games, O’Loughlin says it was his single-minded determination to reinvent himself as a deep key forward in which he finds most pride. 

The young Swan split his early years between the half-forward line and midfield, debuting against the Adelaide Crows in Round 5, 1995 and collecting two All Australian blazers, claiming a Bob Skilton Medal and twice topping Sydney’s goal-kicking before 2004.

But a relentless injury curse would see coach Paul Roos shuffle the magnets on the whiteboard, remodelling O’Loughlin as one of two go-to forwards alongside the colossal Barry Hall.

O’Loughlin averaged 32 goals a season between 1995 and 2003, before his output then shot to 40 as a stay-at-home forward in the years spanning 2004-2009.

O’Loughlin, who'd retire a 303-game legend at the completion of season 2009, believes his career would have fallen a long way short of a triple ton if he hadn’t worked tirelessly to become a deep key forward.

Adam Goodes (left) and Jesse White (right) chair Michael O'Loughlin off the ground.

“The proudest thing about playing 300 games was playing with injuries and remodelling my body to become a permanent stay-at-home forward,” O’Loughlin said.

“That was tough. There were countless hours where I’d find myself training in the dungeon, jumping on the treadmill, going swimming – and I’m going, ‘Sh*t, I want to be out there kicking the footy with the boys!’ But that was my program for the last six years of my career. I had to prepare myself for season after season of AFL footy without doing all the running – and I’m really proud of that.

“There were times where you’d be left in the pool by yourself thinking about all the exercises you need to do to keep fit. I could have easily gone to the café to have a cappuccino or a latte, but you get out what you put in.

“I’m really proud of myself that I was able to change the way I had always played, become stronger, put more weight on and become a permanent stay-at-home forward. The alternative was to retire six years early, but the coaching staff, led by 'Roosy', had full faith I could impact for a long time to come.”

South Melbourne great John Rantall was in the rooms before the game to present O’Loughlin his match guernsey.

The former South Melbourne captain, whose 260-game club record O’Loughlin had surpassed two years earlier, was joined in the change rooms by Peter Bedford and a host of other former Swans.

O’Loughlin then burst through the banner with his two kids, Taya and James, as his mum Muriel, partner Emma, sister, two of four brothers and aunties watched on from the stands. 

“I ran out with my kids and it was just magic. I really loved it and I really embraced it,” O’Loughlin said.

“As a young player you want to get on with your job, play your game, do well and do everything you need to do preparation-wise, but as you get older I reckon you relax a little bit. If you know how the game is played, you’ve done it 100 times, 200 times and you’re about to do it 300 times, you’re a little bit more relaxed. So I was able to really soak it in and enjoy it, and I really wanted to show my appreciation for the fans, the football club and my teammates.”

Michael O'Loughlin sets foot on the MCG with daughter Taya (left) and son James (right). He has since welcomed a third child, seven-year-old daughter Leni.

O’Loughlin posted 19 disposals and two goals in his 300^th game, the crowd erupting as he kicked his first six-pointer and his teammates swamping the milestone man.

O’Loughlin, who’d finish his career with 521 goals beside his name, beat Richmond defender Kelvin Moore in the air, manoeuvred around the Tiger and snapped a goal.

He was then left on the brink of suffocation as his teammates piled on top of him, and the man of the moment told the Sydney Morning Herald post-match it was a snapshot of why the Swans had won the 2005 flag.

“That’s why we won the Grand Final that year,” O’Loughlin said.

“We just have so much respect and pride for each other. I’m just exhausted now and humbled, and thank god I came to this club.”

The man who'd be the best man at O'Loughlin's wedding and the godfather of his kids, Adam Goodes, grabbed the three Brownlow votes for his 25 possessions and four goals, while close mate Brett Kirk was ruthless on his way to 14 tackles.

Michael O'Loughlin midway through one of his 19 dispoals of the day.

The hype surrounding O’Loughlin’s 300^th game on the day made for a blur, and he said the final siren drew curtains on an exhausting week-long lead-up.

“I can’t remember too much of the game, but I’ll never forget the enormity of it after the final siren,” O’Loughlin said.

“Everyone had been wishing me well, sending me messages and saying nice things over the week or so leading up to it, so it was really emotionally draining. You have people ringing to wish you the best, and you pick up every call, text back everyone and return calls and so on, so it was really, really special. Some people you hadn’t seen in 20 years were saying, ‘We’ll be watching, Mick’, and some were in tears.”

The Swans would not feature in finals footy in 2009 for the first time since 2002, marking just the second time Sydney had fallen short of the top eight since O’Loughlin’s debut 1995 season.

But the Swans would storm to their equal-highest winning margin of 2009 in O’Loughlin’s 300^th game, matching their 55-point victory over Port Adelaide at the SCG earlier in the season.

Kirk told the Sydney Morning Herald post-match “there wasn’t much we wouldn’t have done for him today”, saying “he’s such a special person, I love him and he is one of the most loyal friends you could have”.

Goodes and Jesse White chaired him off the ground to the applause of a 32,216-strong crowd, and a world of emotion swells inside O’Loughlin when casting his memory back to the unreserved efforts of his teammates on the day.

“I have hairs on the back of my neck just thinking about it,” O’Loughlin said.

“It gives you goosebumps when you know your teammates, and essentially the guys you’ve grown up with, are willing to run through a brick wall with you. It was unbelievable, and the club did an incredible job of helping me celebrate with my teammates, my family and the fans. I am forever indebted.”

Michael O'Loughlin belts out the victory song with daughter Taya in his arms.

Almost a decade on, O’Loughlin is the founder, owner and managing director of ARA Indigenous Services, a company opening employment opportunities for Aboriginal and Torres Strait Islander communities.

He is also a driving force behind the thriving GO Foundation, an organisation co-founded by O’Loughlin and Goodes in 2009 that provides scholarships to Indigenous students from kindergarten through to university.

O’Loughlin says it means a lot to him to be giving back to his Indigenous community post-footy.

“It was something Adam Goodes and myself were always going to do. I’m very proud of everything I was able to do as a footballer, and I now get to be a role model in the business world,” O’Loughlin said.

“It’s all about working hard and putting yourself out there. Owning a business and working in business is like becoming a footy player; I had no idea what I was doing at 17 but you align yourself with great people and look to them for direction. That really rubbed off well on me as a footy player, and I’ve used the same philosophy as a business-owner and as someone with a number of roles in business.”

Away from work, O’Loughlin and his wife Emma are the parents of three kids: 12-year-old Taya and 11-year-old James, who both ran out with their dad for his 300^th match, and seven-year-old Leni.

The young family live in Sydney’s inner south, just five kilometres from the heart of the Swans at Moore Park, and O’Loughlin’s son James is now striving to one day live out an AFL dream of his own.

The youngster is an under-12 member of the QBE Sydney Swans Academy, which O’Loughlin led as head coach in 2014 and 2015, before passing on the baton to former teammate Jared Crouch.

O’Loughlin said making his 1995 debut set a fairytale in motion, he enjoyed one of the most special days of his career as he notched his 300^th game and – upon reflection of his 24-year journey since arriving at the Swans – he says the fairytale continues to play out.