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It has been over 16 years since a chance outing to Middlesbrough Football Club which started one of the most significant and cherished relationships of Michael Caulfield's career. So much so that he now considers it a friendship.

After calling time on his stint as chief executive of the Professional Jockey's Association in 2003, Caulfield retrained in psychology before embarking on a trip to Rockliffe Park three years' later. 

The opportunity arose thanks to Chris Barnes, Boro's Head of Sport Science at the time, who was first asked by Caulfield if he had any interest in helping Grand National-winning jockey Graham Lee build up his fitness at the club's training ground, an offer he kindly accepted. 

Soon after, the newly-trained psychologist was invited along to watch Middlesbrough train in the lead-up to their historic UEFA Cup final appearance that season. 

'I'd like to think I kept out the way,' Caulfield remembers. 'I just sat quietly in Chris' space. 

'It was the end of the season, the squad were fit and healthy and all trying to get ready for the final in Rotterdam. 

'Bar one player, who was recovering from a slight hamstring injury...' 

The player was Gareth Southgate. 

While receiving treatment for his injury, Southgate enjoyed a 30-minute discussion with Caulfield in Boro's medical room before the pair exchanged phone numbers, promising to stay in touch. 

Yet in the end they not only kept in contact. When he hung up his playing boots, bowing out after a 4-0 defeat in that European showpiece against Sevilla, and jumped straight into his first managerial post with Middlesbrough, Southgate asked Caulfield to join his backroom team.

The sport psychologist role at Boro was his first in football, too. As well as supporting and advising Southgate's players, Caulfield was also tasked with boosting the morale and confidence of his own direct colleagues. 

'I'm not employed by a club,' he explains. 'I consult, because if you're there every day I think that can bring its own tensions. So your role is two or three fold; of course you want to support the players through both difficult and good times, but you've also got to earn the trust and support of the staff, because football staff is expanding by the week almost. They need help too because they feel the pressure hugely.' 

He continues: 'I formed a good relationship [with Southgate] and since I left the club in 2009 I've gone on to do other things. So has he, but we've always, always kept in touch, whether it's for my work in other sports, because he's fascinated by other sports, or his work in football. 

'How he's served English football, not just as a coach, I think he's left a huge footprint. And I always knew from the moment I met him that he was a very, very good person who I wanted to get to know and stay in touch with.' 

The admiration is certainly mutual, which is why they have maintained a close bond after all these years. A testimonial from Southgate about Caulfield, one of the country's most experienced sport psychologists, reads: '[Michael] simplifies sport, understands the changing room and connects with players and coaches from all backgrounds. If you only want science, data and measures, look elsewhere. If you want someone who can make sense of all the clutter that exists in the minds of all athletes and coaches and help them focus on performance, then give Mike a ring.'

Fast forward 16 years from his maiden foray into management and Southgate now covets the country's top job, having led England's national side since 2016. 

Over the past six years he has conducted himself flawlessly, both in front of the world's media and on the touchline, while masterminding England's historic run to a first major final in 55 years at Euro 2020. More still, he was a penalty shootout away from winning it.

Though heading into the Qatar World Cup, Southgate's position is under greater scrutiny than ever before. A string of concerning results over the summer increased pressure on the 52-year-old and even ignited calls for him to be replaced. Some consider him too cautious, too soft a manager to lead an England squad brimming with raw talent beyond this year's tournament.

Caulfield does not see it that way. 'This is a man who absolutely thrives on challenge. And to a degree, proving people wrong, because he's been doing that since he was an apprentice at Crystal Palace. That's who he is.