Back in his playing days, in the 1980s with Brighton and into the ’90s with Huddersfield Town, dreams of such riches and opportunities were so fanciful they barely warranted talking about.
Granted, Brighton were FA Cup finalists in his first season, and the future Republic of Ireland international would be an unused substitute for their Wembley final.
But they were relegated that year and much of O’Regan’s subsequent three years were spent helping the club defy gravity as they began their plummet through the leagues.
He made 86 appearances for a club that plied its trade at the old Goldstone Ground before a move to Swindon and then to Huddersfield, where this versatile young midfielder from Cork would lay down his roots.
Town were a Division Three side at the time, playing at their long-standing Leeds Road stadium, and by the time he left in 1993 a year into the new era of the Premier League, Huddersfield were as far removed from such grandeur as one could imagine.
Fast-forward a quarter-of-a-century and O’Regan will watch with great interest today as Brighton and Huddersfield lock horns with Premier League survival at stake.
“It’s been great to watch this past season, two great little clubs and their fabulous fan bases revelling in Premier League football,” beams O’Regan.
“The whole of Huddersfield, town centre and beyond, has been buzzing all season.
“Everybody is talking about it and for Town to be in this position, with six games to go, when everybody tipped them to be relegated by Christmas, is fantastic.
“And I’ve still got a lot of friends down in Brighton. It’s a special club for me as it was the first club I played for as a professional.
“Like Huddersfield, it’s an amazing the journey they have been on and how far they have come. I still remember going down to play them with Halifax when they were playing at Gillingham’s Priestfield Stadium.
“So a lot of credit goes to a lot of people for transforming the club.”
Having had a taste of the Premier League over the last eight months, the challenge for O’Regan’s old clubs is to now secure a second season among the football elite.
Brighton are three points closer to achieving that goal than Huddersfield, who make the long journey south in desperate need of a positive result as they sit just three points and two places above the relegation zone.
The importance of this game and the next two home fixtures with Watford and Everton is magnified for David Wagner’s team given the enormity of the task facing them in the final week of the season.
First up is a trip to champions-elect Manchester City, before a visit to Chelsea in a game still to be rearranged but expected to be in that final week, and then a home date with Arsenal to finish.
“They’ve given themselves a great chance,” says O’Regan on the 32 games that have gone before. “There may be a helluva tough run-in come the last three games but people shouldn’t forget how well they’ve done to get to this stage.
“A point down at Brighton on Saturday would represent a great result for Huddersfield Town.
“I’m not saying they can’t win or should necessarily set-up to try and get a draw, but a point would also keep Brighton in it and set themselves up nicely for those two huge home games coming up.
“Just look at last Saturday. For a long time that point up at Newcastle, with all the teams below them struggling, would have been a great point, and then they go and concede in the 80th minute.
“So you never know how good a point is going to be and it’s massively important they don’t go down there and get beat.”
Not that O’Regan would advocate the Terriers parking the bus at the Amex Stadium this afternoon.
A team that has scored in only four of their 16 away games in the Premier League next season, cannot afford to be so one-dimensional.
“It will be interesting see how David Wagner sets them up,” says O’Regan of a team that has not scored in their last four games.
“As we’ve seen in a lot of the games when they go down early, Chelsea for instance, it’s difficult to chase when you’re set up to defend and then go behind quickly.
“The big issue obviously is the lack of goals. Again you’d expect Wagner to go with just one man up front but I’d love to see him go two up top for this game, start aggressively and give them something to think about that they perhaps weren’t expecting.
“The two lads at the back for Brighton, Duffy and Dunk, are big lads and will eat up anything Huddersfield throw at them in the air. So Town will need to be a little cleverer around the edge of the penalty area, show some neat footwork and play a few one-twos, which, hopefully, might unlock the Brighton defence.
“The players have got to embrace the challenge and stand up to the pressure.
“I saw Huddersfield beat Brighton earlier on in the season. Town were comfortable and Brighton never really caused them any problems.
“There’s no reason to go down there fearing their opponents or worrying about the statistics.
“Best-case scenario for me, a draw on Saturday and both teams stay up.”