Sheffield United manager Chris Wilder wanted him to stay, and O’Shea was keen to remain in south Yorkshire. But a deal couldn’t be agreed, and the Irishman instead signed a two-year deal with League One club Bury.
The midfielder stayed with the Shakers and it was through their eventual financial implosion in 2019 that he was snapped up by then Brisbane Roar boss Robbie Fowler, and ended up in the A-League.
Meanwhile, the Blades kicked on and were promoted once more, this time to the Premier League, where they have spent the past two seasons.
O’Shea admits it has been difficult at times watching Sheffield United’s meteoric rise and knows he could have been a part of it, but he has no regrets.
“It is just one of those things,” O'Shea told The World Game.
“I’m not going to lie and say there wasn’t moments I thought maybe I should have signed it, but at this time I’ve got no regrets because I’m in Australia now and I’m not sure that would have happened if I went there. And I love it here, I love the football here and me and my family are really happy here.
“There were times that I did regret it – I remember my first season at Bury, that was the season I turned the offer down and went to Bury.
"I got injured on my debut and I tore my medial ligament in my knee and that put me out for three months, so while I was injured, (I thought) 'why have I come here, this has been a mistake'.
“And while this is all going on, Sheffield United are starting to doing really, really well so I’m watching the games, I’m injured and I’m thinking, 'what have I done, I’ve made a big mistake here'.
"But that’s just football. We couldn’t agree. We shook hands, I wished them the best of luck, there was no hard feelings at all.”
O’Shea describes his time working under Wilder at Bramall Lane as “brilliant”.
“The biggest thing for me was that Chris Wilder was a big Blades fan and so was Billy Sharp,” he said.
“But that alone, it just created this culture where anyone who walked in the door, they just instantly became fans because it’s bedded into you from the manager, the captain, all the staff of the club.
"You literally went in and all the players to this day all call themselves Bladesmen.
“It was amazing and I wasn’t surprised at all to see what they did a couple of years after to get promoted to the Premier League. Obviously they had a great season in the Premier League last year and they deserve all the credit. They were excellent.
“They were brilliant with me as well, I really enjoyed my time there. We just couldn’t agree on a contract in the end and I ended up leaving. They did offer me a contract but it just wasn’t meant to be at the time and we couldn’t agree.
“I was actually very disappointed at the time that we didn’t agree because I loved my time there and they did go on to do really well, and it was actually hard to watch them getting into the Premier League from afar. But they deserved everything they got.”
The Irishman’s move to Australia came about through Fowler two years ago when Bury went bust. O’Shea also was buoyed by receiving favourable advice about the A-League by compatriots Roy O’Donovan and Andy Keogh.
“I was playing for Bury and unfortunately they fell into financial difficulty,” the 32-year-old explained.
“The players had stopped being paid. I’d had a good season and had created a bit of interest, which had alerted Robbie Fowler who was going to be the manager of Brisbane.
"So I had a call from Robbie because he knew the situation at Bury was getting worse and they were on the brink of folding.
“He made contact with me, I spoke to my wife and it was something that we wanted to do. I obviously spoke to some of the Irish lads out here like Andy Keogh and Roy O’Donovan about their experience out here and they had nothing but good things to say.
"I’m really glad that they directed me this way because I’ve loved every minute of it so far.
O’Shea has hit the ground running in Queensland and has become an integral part of the Roar. This season the midfielder has made 12 appearances, scoring one goal and has created the sixth-most chances in the A-League with 33.
“That’s just the type of player I am, I’ve always tried to be a creative player,” he said.
“Even though I’m creating those chances, I’ve got zero assists so that might not have been as good chances as they could have been to be honest.
"I just try to get on the ball as much as I can and I think Robbie Fowler and Warren Moon have both given me the freedom to get on the ball as much as I can and try and make things happen.
“That’s obviously part of my role as a player and I really enjoy it. This season I’ve had to play a bit deeper than what I would like and what I have played in recent years, but I’ve enjoyed it. At the age I’m at now, I still feel that I’m learning.”
Brisbane are currently in ninth spot on the table with four wins, four draws and four losses from their 12 fixtures. O’Shea is desperate for the Roar to turn things around and start climbing the ladder again.
“This season we started really well and we’ve had a bit of a slump now, we haven’t won for seven,” he admitted.
“It’s up to us now to get out of that. We know what the table’s like, you win a couple of games and you can get back in the mix again. But something’s got to change really soon for us as it hasn’t been good enough.
“We haven’t been scoring goals and we’re actually quite lucky we got the four wins in a row at the start of the season because we’re not too far afoot.
"But if we didn’t get them we wouldn’t be. We’ve played a few different formations this season and there’s been a bit of rotation in the squad as well.
“So it’s never really a good sign when the team keeps changing, obviously a manager would like to have a set eleven, and usually when you’re not changing your team things are going well.
"But that’s down to us, we need to get it right and make the manager’s job a bit easier.”
O’Shea might be a long way from his home town of Dublin but he has adjusted well to life down under and in February signed a new multi-year deal with Brisbane.
The former Chesterfield and Bury man is already planning to stay in Australia to live when his football days are eventually over.
“I’ve loved it, absolutely loved it here,” he said.
“I wouldn’t have extended my stay at Brisbane if I wasn’t really, really enjoying it still. Obviously the first year was a little bit easier as there was no COVID-19 and the start of the season was really enjoyable.
“But then COVID hit and we’ve been here as a family on our own, so we are starting to miss family back home.
"But football-wise I’m still absolutely loving it. I can see myself staying here now and retiring in Australia – that’s the plan anyway. I love the football here, the people have been so nice to us.
“It’s been a really enjoyable experience and we just can’t wait for the world to go back to normal.”
