Sol Campbell suffered penalty-shootout heartache at four major tournaments with England - and he fared no better on his managerial debut with Macclesfield.
The former England star had no doubt dreamt about managing at the likes of St James' Park when he set out in search of a job six years ago - and here he was making his belated bow, albeit in front of 1,126 in the second round of the Checkatrade Trophy.
Campbell looked the part in suit and tie but The Silkmen were not as smart from 12 yards and, after striker Scott Wilson salvaged a 1-1 draw to cancel out Elias Sorensen's first-half opener, Ben Stephens was the fall guy in the shootout. For the record, this was the club's first defeat on penalties in their 144-year history.
'Sometimes it's good to get these sorts of things out the way,' laughed Campbell afterwards.
'But I really enjoyed it. We showed great heart and fought for every ball. I've only been here a week so I had to implement things quickly and the players responded.
'They got it down and played, we just needed more confidence in front of goal, but that will come.'
It was on Tyneside that Campbell played his last football under Alan Pardew seven years ago. His final appearance at St James' was a 3-1 victory over Liverpool with a sell-out crowd watching on.
This, then, felt very different. Every instruction barked was audible from the stands, and he did not hide his displeasure with a 's***' corner early on.
Campbell manned his technical zone throughout and used a pen - fidgeting and chewing - as a means to alleviate this newfound stress.
'I've had to keep knocking on the door to get this chance,' he said, his new club currently bottom of League Two. 'You can get to a situation where you wonder if it will happen.
'But I am relishing the challenge. I'm going to get my hands dirty and hopefully the players will respond to that and see I'm in there with them. Every game is a cup final for us now.'
It took half an hour for the visitors to register a shot on goal but Koby Arthur's weak curler won little acclaim from his boss.
Campbell would have soon realised the size of the task facing him, especially when his defence failed to deal with a left-wing centre and allowed Sorensen to poke home from close range on 23 minutes for his 18th of the season.
Macclesfield were better after the break and their 'gaffer' - as the players addressed him - was certainly more animated, even trapping one dropping ball with his dress shoes - perhaps he felt the need to justify his comments about being one of the best players in the world during his unveiling last week.
His players responded and they drew level when Wilson scampered clear and lifted over Nathan Harker six minutes from time.
But Campbell would have known all too well that feeling of spot-kick despair.