In late May 1999, New York took part in the Connacht Championship for the first time. A 3-13 to 0-10 defeat to a Mayo side who had reached two of the previous three All-Ireland Finals was nothing to be sniffed at.
Indeed writing in the Irish independent at the time, Offaly's All-Ireland winning manager Eugene McGee said the performance by the Exiles suggested they could beat "up to a dozen" inter-county teams in the country at the time.
For the first three years they travelled, ever since the long-haul journey has been made by the other Connacht teams. Twenty years later and they still await their first win.
It is easy to overlook the fact there have been a number of near misses. In 2003, Sunday's opponents Leitrim required extra-time to get the job done, while seven years later, Galway's 1-02 in injury-time put the gloss on a seven point victory.
Two years ago, Kevin McStay's Roscommon reign got off to a nervy start when the Rossies advanced by the bare minimum.
As @NewYorkGAA take on @LeitrimGAA this weekend, GAANOW Rewind takes a look back to 2016. New York ran close to @RoscommonGAA; only losing out by one point on a score of 0-17 1-15! pic.twitter.com/lXwrdZrCYm
— The GAA (@officialgaa) May 2, 2018
Some heavy defeats which have peppered their existence has often been the rod to beat the Exiles with. Sligo racked up 3-21 in 2012, while 12 months later, on their last visit to the Big Apple, Leitrim beat them out the gate by 28 points.
Manager Justin O’Halloran has been involved since the experiment began and spoke honestly this week about where New York find themselves in the pecking order and what they hope to achieve. With no qualifier avenue open to them, it is once again all or nothing first time out.
Former Mayo defender Tom Cunniffe will lead the side out at Gaelic Park (throw-in 7.15pm Irish time), while Armagh’s Jamie Clarke will be the focal point in attack.
O’Halloran knows the task is a sizeable one, but there is belief in the camp that Sunday, 6 May, could be their day.
"Leitrim are the best team on our calendar," he told RTÉ Sport. "We have never beaten them. We are the underdogs. We don’t talk of an upset, even though we are confident of winning."
Brendan McGuckian's side are the lowest ranked Connacht side New York can face, and their Division Four form makes it hard to evaluate their standing.
They began with three defeats - a creditable showing against eventual champions Laois sandwiched in between 10 and 12-point defeats respectively to Antrim and Carlow. The weather put paid a trip to London, while the game with Waterford also failed to see the light of day.
A 2-15 to 0-10 victory over Wicklow was a decent way to finish off a topsy-turvy campaign.
A New York win would cause ripples - the players are acutely aware of the opportunity presented to them -though it might not be as unlikely a prospect as some would be led to believe. According to most bookmakers, there is a more likely chance of a home win in the Big Apple than a Galway win over Mayo the following week.
The significance of a win cannot be underestimated.
"It would probably be my best day on a football field ever," O’Halloran admits. "A win would be huge, absolutely huge. I have a young wife, and thankfully my wife is very on board with me doing this and my kids are very proud of me.
"I wouldn’t be here if I didn’t think we could win."
Training began back towards the tail end of November, with training programmes issued ahead of the Christmas season. It was also a chance for players to familiarise themselves with the 2018 squad. According to Cunniffe, just six of last year’s starting team remain.
"A lot of guys left at the end of last summer. We have a nucleus that live here, and are still here. We were starting from scratch again," O’Halloran explains.
From January on, training was ramped up to three nights a week.
While Storm Emma and Hurricane Ophelia wreaked havoc on sporting events here earlier this year, weather conditions play a significant role every year for the Exiles.
"Weather wise we have been lucky enough. We didn’t get a lot of snow, but it has been very cold. There were a lot of very cold nights, but still able to train away."
"We have been playing in-house games for the past two months, so it had been getting a little bit stale, the same guys marking each other"
Contrary to some perceptions, O’Halloran refutes the suggestion that it must be a challenge to motivate his players to slog it out during the harshest conditions for just one crack at the Championship, regardless of the result.
He has voiced his displeasure before that the qualifiers aren’t an option, but that doesn’t impact the players. Should Leitrim fall to a defeat on Sunday, they will be drawn against one of the other 16 counties to lose a first-round match in a preliminary qualifier.
"I don’t think it is a hard sell at all," he says.
The visit of the All-Ireland club champions Corofin last week was far more reaching than just your average challenge game, albeit it a very long-distance one.
Full time!@CorofinGAA 1-7
— New York GAA (@NewYorkGAA) April 27, 2018
New York GAA 1-20
Thanks for coming down everyone and thanks to @IrishVoiceGP for the live updates! #GAA pic.twitter.com/5eqagIkePs
O’Halloran acknowledges that All-Ireland celebrations, the journey involved and the fact that the Galway club were without a number of players all contributed to the 13-point victory for his team, but it was about much more than simply the result or even performance.
"We have been playing in-house games for the past two months, so it had been getting a little bit stale, the same guys marking each other. It revamped the camp and we feel good after it."
Most neutrals will be keeping tabs on what Clarke can bring to the party for the Exiles.
The gifted forward provides the clinical finishing ability that has perhaps cost the underdogs dearly at times in the past. Most managers shy away from the temptation of heaping praise on individuals, but the addition of star quality is a massive boost for their chances.
"Jamie would bring a lot to any table. He’s a great outlet for us and played well against Corofin.
"Leitrim are going to have to pay a lot of attention to him. Even if he doesn’t get a score, he’s bringing defenders out of the way for our other forwards, which is a huge boost to us."
Leitrim-born Fergal Ellis is likely to face his native county, while two New York born players, Shane Hogan and Mike Cregan are "there or thereabouts" to start.
Sunday marks the 90th anniversary since the first game was played at Gaelic Park, and hopes are rising that another piece of history will be created this weekend at the Bronx-based ground.
Follow all the action from Gaelic Park via the live blog on RTÉ.ie and the News Now App or listen to live radio commentary of New York v Leitrim on RTÉ Radio 1's Sport Extra from 7pm.
