Ciaran Caldwell joked it is "sod's law" that he could miss Crumlin United's huge Irish Cup clash with Larne because he will be on a pre-planned holiday.
Caldwell's side will travel to Inver Park in the fifth round of the competition on January 7.
The former Irish League midfielder ended his senior playing career with Larne before taking up the reins as player/manager with Crumlin.
Read more: Caldwell recalls hilarious Izaguirre 'face plant' moment against Celtic
The 33-year-old - who won back-to-back Premiership titles with Cliftonville - admits he might have to "sweet talk the missus" to fly home for the game.
Alternatively, he will have to watch a stream of the game and stay in touch with his backroom team over the phone.
"It is a pre-planned break. I will be away on holiday at the time, but I might look at trying to get back for the game," Caldwell said.
"I booked it with my missus because Crumlin have never made the fifth round of the Irish Cup. We haven't made it in 15 years, so it is sod's law that we do it the year I book a trip away.
"I might have to sweet talk the missus into allowing me home for the day, but that could be a hard sell.
"If I don't make it back I will watch a stream of the game, and I will constantly be on the phone to the boys.
"I wouldn't be playing anyway. I always feel it is important for the players, and the local lads who give it their all for Crumlin, to play these games. It is for them.
"They can wear the jersey with pride."
Caldwell admits he had mixed feelings after landing the current Irish Premiership leaders in Tuesday's fifth-round draw.
He said: "You either want one of the big boys, or a team you can possibly get a result against and progress in the competition. Well, we have one of the big boys.
"But it will be a great experience for our players. We played Larne in pre-season, but this will be a completely different level.
"It will be a learning curve for us. We have played aged 17, 18, 19 and they will learn so much from this.
"We have a young player Conall Cunningham who has scored in every round, and he is only 18. That is a massive achievement.
"We had our Christmas do and someone said to him about it being a great achievement scoring in the fourth round, and he reminded them that he had actually scored in every round.
"He wouldn't be too shy, but he is a young lad who had to get out of school to attend today's draw. This is all experience for him.
"Hopefully he scores again on January 7. The only problem might be keeping them out at the other end."
Caldwell left Larne in 2018 with the Inver club's full-time approach influencing his decision to leave.
A few weeks later he was appointed Crumlin United's new player/manager, with the former Premiership title winner cutting his managerial teeth in the Amateur League.
"I finished my Irish League career at Larne. When I was there they treated me so well and I am a big supporter of them," Caldwell added.
"At the minute we are going down to play the best team in the country, so hopefully we get as many fans down as possible because we will need them."
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