Back in 1997, a defeat away to Young Munster brought the curtain down on their time at that level, beginning a journey which would eventually take the Dublin club through Division 2 and Division 3 rugby in the league's older formats.
This weekend, that long road finally leads them back to where they have wanted to be. Old Wesley will begin their first Division 1A campaign in 29 years with a trip to Castle Avenue to face Clontarf, opening a new chapter for a club determined to ensure promotion last season was the beginning of something rather than the destination.
And leading them into that new era will be a captain who was not even born the last time Old Wesley played top flight rugby. At just 21 years of age, Billy Corrigan has been entrusted with the captaincy for one of the most significant seasons in the club's recent history.
The towering 6ft 6 lock has already represented Leinster and Ireland during an impressive young career, but Old Wesley has always carried a particular significance for the Wicklow native.
Born in Wicklow and educated at Powerscourt National School and Presentation College Bray, Corrigan played his mini rugby with Old Wesley. He returned to the club after leaving school and is now entering his fourth season with the senior side.
Captaining them into Division 1A therefore means considerably more than simply wearing the armband.
“I'm immensely proud of it to be honest” Corrigan said.
“I played minis in Old Wesley and the last three years playing rugby here have been such a pleasure. And then to have people like Kieran (O'Shea) alongside me makes it so much easier.
It alleviates a bit of pressure being a young captain when you have lads like Kieran and other big figures like Stephen Smyth and stuff that kind of help you along the way. But yeah, it's something I'm so proud of, especially as we said, going back into the first 1A season in nearly 30 years.” he added
That sense of history is impossible to escape around Old Wesley.
Corrigan may not have experienced the club's successful period during the 1990s himself, but he has heard enough about it.
The stories have been passed down by those who were there. The reminders of what Old Wesley once achieved have never been too far away, particularly for a generation of players attempting to bring those days back.
“I mean there's so many games where you get a slap on the back and you're told about the glory days” Corrigan explained.
“It's my fourth year in the club now, it really drives you on and makes you want to be in that position. Because the club's been knocking on the door for so many years now and we know if you look around the facilities we have available to us, this should be a 1A club.
So now it's just on us as players to live up to everything that we've been provided with and make the most because there's definitely the talent there.”
Old Wesley certainly had to wait and earn their return. Promotion from Division 1B had become an increasingly significant objective after years of pushing towards it without quite getting over the line.
Last season everything finally came together.
Fourteen victories from 18 league matches delivered the Division 1B title and, with it, automatic promotion. After years of knocking on the door, Wesley did not require a playoff or one final roll of the dice. They finished on top by a single point and earned their place among the country's leading clubs.
For Corrigan, the achievement also carried echoes of another important Old Wesley promotion.
Ten years earlier, the club had climbed from Division 2A into 1B. Many of the players involved in that success remain close today, something the current squad used as inspiration while creating their own piece of history.
“It’s something that we kind of themed ourselves on last year, was that it had been 10 years since the club's last promotion from 2A to 1B, and the fact that that team is still so close around each other now.
Now you're nearly 30 years on, so it's something that we'll look forward to this year and being able to build ourselves on. Because if you look back at that team, there’s some incredible players and we just want to be able to kind of live up to the highs that the club reached in the 90’s.” he continued.
There will be little time for Old Wesley to ease themselves into their new surroundings.
Clontarf away represents about as difficult an opening examination as Morgan Lennon's side could have been handed.
The north Dublin club reached last season's Division 1A decider before suffering defeat, and Castle Avenue has long been one of the toughest destinations in the All-Ireland League.
Remarkably, despite the long histories of both clubs, this weekend will mark their first meeting in the All-Ireland League. They will not however be complete strangers.
Old Wesley travelled to Castle Avenue in the Leinster Senior Cup last month and were beaten 52-33 by Clontarf, giving Corrigan and his teammates an early indication of the standards required.
Their other cup performances have provided plenty of encouragement.
Wesley defeated fellow Division 1A outfit UCD 24-12 away from home and also recorded an impressive 24-17 home victory against reigning cup champions Lansdowne, handing them their only defeat of the competition.
Those games have allowed the newly promoted side to test themselves against the calibre of opposition they will now face every week.
Corrigan is under no illusions about the size of the opening challenge.
“There's no bigger task than Tarf away, but look, it's something that we've been so excited for” he said.
“Not just this pre-season, but last season we would have said we have to hold ourselves to the standards of a 1A team and now we have to hold ourselves to the standards of a top four 1A team, and one of the best ones in Clontarf at that.”
That change in language is significant.
Old Wesley do not want to spend this season viewing themselves simply as a newly promoted club delighted to be mixing with the country's best again. They spent last season preparing themselves for this level before promotion was even secured.
Now that they have arrived, the standards have moved again. For Corrigan, it is about discovering how far the group can push rather than being satisfied with simply ending the club's long absence.
There will certainly be no shortage of occasions to embrace. Division 1A brings with it a collection of major Dublin derbies and some of the most established names in Irish club rugby. For a player who has heard about Old Wesley's previous top-flight days since returning to the club, these are precisely the fixtures Corrigan wanted to experience.
“Well there's plenty of Dublin derbies this year” he said.
“You don't aspire to be a 1A team to not play these days. These days are the exact ones that you look forward to and obviously, like you say, it's a tough task, but it's something that we've been practising for.
“We talked about it in the huddles since I arrived in this club, since I left school and I suppose, like I said, we're not holding ourselves to the standards of what we were last year. We played some brilliant rugby, but it's about putting our own stamp and impression on the league this year and kind of showing what this club's about and what Morgan's built now for over 10 years.”
Head coach Lennon has overseen much of the gradual progress which has brought Wesley to this point.
Promotion did not arrive overnight. The structures, standards and expectations have been developed over a prolonged period, and last season's title was the reward. The challenge is now to carry that momentum into Division 1A.
Perhaps nowhere will the significance of promotion be more visible than at Energia Park. Towards the end of last season, as the possibility of winning Division 1B became increasingly real, attendances began to grow. The club's minis came to watch, families gathered around the pitch and a sense of momentum developed.
Corrigan noticed it. He is already looking forward to the moment when he gets to lead Old Wesley onto their home pitch as a Division 1A side for the first time.
“It's something that I haven't thought of hugely yet, but if I look at the back end of last season and the momentum we picked up and we were drawing some really big crowds and it was great to see the minis involved and they were always at the games and stuff just because we were doing so well.
“So to be able to lead the lads out and through that big crowd, because we're at the top of that momentum swing now, so if we can go out and put a big stamp on that first home game, it means so much for the club. And then for me personally to be at the forefront of that and holding the mascot's hand is huge.”
It is a striking image for a player whose own journey began as one of those minis. Corrigan once represented the youngest generation coming through Old Wesley. Now he will be the senior captain those young players watch from the side-line.
He is still only 21 himself, an unusually young age to shoulder the responsibility of captaining an All-Ireland League Division 1A club, but he is surrounded by experienced voices. That combination of youth and experience will be important as Wesley navigates unfamiliar territory.
There will inevitably be setbacks. The standard will be higher, mistakes will be punished more severely and every weekend will bring another demanding assignment. Corrigan, though, believes last season taught the squad an important lesson about how to handle a league campaign.
Previously, Old Wesley had attached numbers to their ambitions. Win a certain amount of games and promotion should follow. Last season they moved away from that approach and concentrated instead on the immediate challenge.
Fourteen wins followed anyway. It is an approach they will retain in Division 1A.
“It is the cliché, but it's game by game” Corrigan said.
“Like two of my 1B seasons, we went out and we kind of put a quantitative figure, like we win 14 games and we win the league. Last year it was week on week. You take every opposition as they come and you treat them with the same respect and it's no different this year.
We look at Tarf, we build ourselves into the best position we can for Tarf and then after that it's Con and we reassess them after that. But yeah, I know it's a cliché, probably not what you want, but that's the only way to approach it I feel.”
So Clontarf comes first. There will be time later to consider where Old Wesley sit in the Division 1A landscape and how realistic their ambitions might be. For now, there is a first top flight league fixture in 29 years to play.
For the older generations around Old Wesley, Saturday will bring memories of the club they remember from the 1990s. For Morgan Lennon and those who have spent years building towards this moment, it will represent another significant milestone.
And for the current players, it is an opportunity to begin writing their own story rather than simply hearing about those that came before them. At the front of it all will be a 21 year old who was not born when Old Wesley last competed at this level.
Billy Corrigan has heard plenty about the glory days. Now, as captain of Old Wesley in Division 1A, he has the chance to help create some new ones.
By Diarmuid Kearney