Jim Ervin's Irish Cup story contains the full range of emotions.
The Belfast man lifted the trophy on four occasions at Linfield but he also missed out on two finals.
A cruciate injury kept him out of the 2008 final against Coleraine, which David Jeffrey's side won 2-1.
And the right-back was deemed surplus to requirements in the 2-1 win over Portadown in 2010.
But Ervin's Irish Cup tale has just taken another dramatic twist.
With memories of a glorious nine-year spell at Windsor Park still fresh in the mind, today he will be aiming to crush the Blues' cup dream while wearing the colours of his new club, Ballymena United.
The 28-year-old's first challenge at the international venue will be to make his way towards the right dressing room. Of course, Ervin is in good company – he isn't the only Linfield legend returning to haunt the Blues.
Sky Blues chief Glenn Ferguson and his backroom team of Lee Doherty and Norman Kelly also return to familiar surroundings.
And they aren't returning for this sixth round tie just to make up the numbers.
The stage is set then for Ervin to pop up in the last minute to score the winner.
"I'm going to approach this game as I would any other," said Ervin.
"Yes, it will feel strange running out at Windsor for the visiting team but I'll conduct myself in the way I always do and I want to win the match. Going into the right dressing room might be my first challenge but after that I have a job to do for United.
"I know a lot of the Linfield players, some more than others, but when you face the top sides whether it's Glentoran or Portadown you have a good understanding of who you are up against and their strengths.
"David (Jeffrey) will have his team well prepared to do a professional job but it's a one-off cup game and with the squad we have we are capable of beating anyone if we are on form.
"We have been unfortunate against the bigger teams recently and perhaps when you are playing these teams it is harder to get the right decisions but we will give Linfield a game, I'm confident of that.
"I work with Damien Grant who was Ballymena United's goalkeeper in their 1989 Irish Cup win and he keeps reminding me of his heroics.
"He kept Linfield at bay in the semi-finals so maybe it's my turn to be the hero!"
Ervin agreed a two-and-a-half year deal with the Sky Blues last month and he's waved farewell to reserve team action at Windsor Park to embrace the cut and thrust of the Premiership again.
"The reality for me is that I'm 28-years-old and I still feel I can contribute a lot and win trophies hopefully," he added.
"I felt that at my age I really needed to be playing as much first team football as possible.
"Big games have come quickly and when you are playing Saturday-Tuesday that doesn't leave much time to sit around and reflect on the move.
"What you get with Glenn (Ferguson) is someone with a wealth of experience and knowledge and the training has been top notch.
"I had been at Linfield a long time and perhaps that freshness and new challenge is just what I needed."
* Ballymena United president and main club sponsor Norman McBurney received his OBE yesterday at Buckingham Palace.