Crawley Town boss John Yems hoping to haunt Leeds United's Victor Orta and Angus Kinnear
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Had events turned out differently, he could have been trying to help the Whites through.
Yet the manager who had a job interview with the Whites is now firmly fixed on subjecting the club to another cup upset and stressing that anything is possible in the third round showdown.
Leeds and Crawley will meet for the first time ever in Sunday's 1.30pm kick-off at Broadfield Stadium and there are very few links between the two sides.
Yet the man in the home dug out will actually be looking to inflict a cup upset on a club he thought he was set to work for.
Having left Bournemouth where he was part of a three-man coaching team alongside Eddie Howe and Jason Tindall, Yems made the long trek up to Yorkshire looking to land a job on the Whites staff under director of football Victor Orta in the summer of 2018.
Yems felt his work with the Cherries and previous feats with the likes of Exeter City would stand him in good stead. Indeed, the 61-year-old Londoner felt the job was in the bag.
It wasn't, and the journey to meet the likes of Orta and chief executive Angus Kinnear was to prove a one-off visit with Yems unsuccessful in his application.
Instead, just over one year later, Yems landed himself a first job in outright Football League management at League Two side Crawley where he had been joint caretaker boss before.
Fourteen months after taking the job, Yems then saw his side handed a third round FA Cup tie against what could have been his own employers.
The Crawley boss says he is now looking forward to meeting Orta and Kinnear in different circumstances - though deep down the Red Devils boss hopes the Whites duo will actually be in no mood to talk come Sunday afternoon.
"I text them on Wednesday and it will be good to catch up with them," said Yems, asked about Orta and Kinnear.
"It's funny what football throws up where you know people all the time but let's hope we are not talking to one and another at five o'clock because we have won and they haven't.
"I knew Angus vaguely when he was at West Ham.
"And with Victor I went up to Leeds for a job after I left Bournemouth which I thought I had but the gits never gave it to me.
"Because we had the experience of when I got Callum Wilson and people like that to Bournemouth and I worked with Ed and I brought Eddie and Jason back to Bournemouth and we had a three man team there.
"I went on and was the assistant to Paul Tisdale at Exeter.
“The promotions and the levels of the leagues - at the time, Victor and that didn’t have no-one who knew them sort of levels.
"It would have been good to get involved with them.
"I went up there and met them all and I have got relatives who live just outside of Huddersfield so I know the area reasonably well.
"But it is a long old slap from London and the way they talk up there it might take me a year to get used to it."
Instead, with his application declined, Yems is now just over one year into his role at League Two side Crawley.
At current progress, he and his Red Devils side could be heading to League One with United's forthcoming FA Cup opponents unbeaten in nine games, five of which have ended in victory.
Crawley also have history where FA Cup runs are concerned with the West Sussex side having reached the fifth round of the competition in both 2010-11 and 2010-12 under a man who would go on to be United's manager in Steve Evans.
As a Conference side, Crawley's 2010-11 run was ended with a 1-0 defeat at Manchester United whilst Stoke City ended the adventure the following season with a 2-0 triumph in West Sussex.
Leeds, on the other hand, have fallen at the first hurdle in 12 of their last 17 FA Cup bids with Newport County, Sutton United, Rochdale, Histon and Hereford United all responsible for causing major cup upsets against the Whites.
"Me personally, having been in the game as long as I have, nothing ever surprises you and you shouldn't be expecting anything," said Yems, reflecting on whether the contrasting cup histories of both clubs could have any bearing on Sunday's game.
"It is what it is, it all depends on who fancies it on the day, whether the wind is blowing the right direction or the referee has another drama that others don't have.
"There's all sorts of things that can happen and you just hope that it falls in your favour rather than the opposition but it won't be for us not wanting to and for not trying to get a result because we will be,"
Pressed on what Leeds can expect - with old friends Orta and Kinnear looking on - Yems said: "Just an honest side that will be looking to play.
"We are not going to come out and just keep lumps out of you because I don't think we would be able to catch half the players to do that to be honest.
"But we want to stay in the game, we want to be competitive and very enjoyable hopefully.
"It will be an enjoyable game, even more so when we do get a result though I am tempting it a bit there.
"But we are just a hard working side that try and play football, we have got some very good players and I think you will be pleasantly surprised.
"It's a tough game, let's not dress it up but there's loads of other things that have happened in the past that shouldn't have.
"Maybe this might be one day where the Gods shine on us for a bit."
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Thank you Laura Collins