Rangers fell to a 2-0 defeat away to Union Saint-Gilloise on Tuesday as their bid for a place in the Champions League hit a bump in the road - and the Belgian club standing in their way boast a very talented Irishman behind the scenes.
The return leg of the third qualifying round tie is set for Ibrox next Tuesday, with the winners progressing to the playoff round where they will face either Monaco or PSV Eindhoven.
But just who is Union's Sporting Director Chris O'Loughlin? Here is all you need to know about the high-flying Irishman.
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O'Loughlin was born in Limerick to a father from Belfast and a mother hailing from Scotland, while he spent much of his childhood in South Africa.
He played for Cliftonville and Larne in the Irish League before his playing career was curtailed by injury. That didn't kill his appetite for the game of football, however, and a pathway into coaching was soon carved out.
O'Loughlin ventured towards coaching rather unexpectedly, with a move back to Ireland coming after he finished school. Not long afterwards, in 2004, he got involved in junior coaching and thus the long road to Union had begun.
He had secured a UEFA B licence by the time he returned to South Africa, before a good deal of networking led to him meeting Congolese Belgian Bibey Mutombo, who was coaching Black Leopards in a rural and remote part of South Africa. Mutombo soon began coaching Orlando Pirates after their meeting and O'Loughlin saw an opportunity to make further inroads.
He subsequently made it his business to attend a Pirates game, compile comprehensive notes on what he saw and make an effort to get them to his old friend.
It didn't look promising initially as staff at the Pirates' facility rebuffed the Limerick man, but Mutombo had the final say as he recognised O'Loughlin even after five months apart and welcomed him in to share his work.
An invite was extended for further discussions and that snowballed O'Loughlin's attendance at various training sessions and second-string games before Mutombo asked him to be his assistant coach with the first team.
He then took up a coaching role at the Supersport academy in South Africa before arranging a week with Espanyol followed by the same with Valencia - where he bumped into one Marcelo Bielsa.
A stint in charge of Congolese side AS Vita came next and O'Loughlin had his side on a positive run in the 2009 CAF Confederations Cup before a politically-motivated chess move hampered him.
A solid run in the competition set up a game they could not afford to lose against Santos from Angola; a semi-final berth awaited them if they won or drew the match.
However, one day prior to the big game, O'Loughlin was informed that he would not be able to obtain a visa to travel with the team. It threw a massive spanner in the works given the fact that he had not been operating with his own assistant coach. In the end, the football federation installed a coach of their own choosing to oversee the game.
After leaving in acrimonious circusmtances the first time, a second stint in Africa came before O'Loughlin travelled around a bit more.
Before the Union call came, O'Loughlin spent five years with Sint-Truiden either side of short-term coaching roles with Charlton and Kortrijk.
Brighton owner Tony Bloom and Alex Muzio recently bought the Belgian club and they propositioned O'Loughlin; he was offered a move away from the trenches of the dugout and upstairs to the role of Sporting Director.
And it is a role he has relished.
In an interview with the Irish Times earlier this year, he said: “I never thought I’d be a coach, then I thought that would be all I do, but this is a great position.
“It’s a great role, but it helps when you work with a good president like Alex Muzio, who is heavily involved on a daily basis, and a good CEO.
“The vision is aligned across the board, which is the dream scenario.”
And the positive impact he has had on the club can hardly be denied at this point; Union topped the Belgian Jupiler Pro League standings last year, which put them in a strong position in European qualification terms.
Due to the playoff format which ensues between the teams finishing in the top four in Belgium, Union lost out on becoming champions as Club Brugge claimed four wins and two draws to secure the title and qualify for the Champions League group stage.
Union finished in second place, however, and it is that strong domestic form that has earned them a crack at well-established sides like Rangers - and they are now halfway towards dumping the Glasgow giants out.
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