The majority of hoary old managers will not live long enough to lift the FA Cup. Nor will they work in the Champions League. Nor will they work in the Premier League, the Championship or League One. It sounds like the stuff of which dreams are made, but there may yet be one more significant step on 'Dima's' journey to self fulfilment.
Before the last European Championship finals in Austria and Switzerland, Di Matteo looked likelier to be working on his chipping rather than a Champions League final against Bayern Munich. In spending lunch interviewing the (interim) Chelsea manager overlooking the 18th green at the Abu Dhabi golf championship, Di Matteo was busy trying to calculate where would be best for him to open out in the undulating world of coaching.
Haggard and somewhat hairy European coaches in the form of Laszlo Boloni, Bruno Metsu and Winfried Schaefer were all picking up a golden pay cheque working for the football-fascinated oil barons of the UAE around the same time - a path once trodden by the former England manager Don Revie in the 1970s - but these men were all gnarled veterans. By comparison, Di Matteo was not even a novice. Not even qualified for the start in coaching he sought.
A stint of pro-celebrity golf with Prince Andrew here and there is gratifying and an appearance on a revamped Superstars on Channel Five was jovial enough, but nothing quite gets the juices flowing for a footballer like working in the world game. This was a figure starved of the sensation since the tremors of a triple leg fracture forced his retirement at the age of 32 around 2002.
In discussing the prospects of Roberto Donadoni's Italy at the Euro 2008 finals, Di Matteo disclosed an admiration for Arrigo Sacchi, a figure who remains the last coach to win back-to-back European Cups at Milan in 1989 and 1990. During his peak years representing Lazio, Chelsea and Italy, the bounding midfielder Di Matteo snagged 34 caps for the national side between 1994 to 1998. He knows quite well the benefits of getting tactics right.
"Sacchi is the best manager I've worked under," said Di Matteo. "Sacchi was like a professor, like a teacher. He was very effective in teaching players what they had to do to improve after games.
"Everything had to be perfect under Sacchi. If you stood out of position for only half a yard, he would be upon you. You do feel the pressure in the coaching game, but you deal with it."
Chelsea's win over Barcelona in the Champions League semi-finals would have contented the professor. Sacchi set up a road blockade that nullified a Brazilian side in the 1994 World Cup final that contained Romario and Bebeto. 90 minutes and 30 minutes of extra-time in a boiling Pasadena may have been a huge disappointment to the worldwide audience of millions, but good defence is as much an art form as a scattergun attacking approach.
Roberto Baggio lifted a penalty over the bar in the shoot-out in Italy's defeat after a sterile 0-0 draw, but Sacchi's stoppers, led by Franco Baresi and Paolo Maldini, had stood the test of time in normal time.
From a coaching perspective, it was a demonstration of how organisation can win the day in any match against a supposedly superior calibre of opposition.
"Few teams work as a unit - few, really few teams," says Sacchi. "They are all made up of little groups. There is no great connection, nor a good distribution of players around the pitch."
Italians have presided over a real pride in organisation, the ability to find a formation that enables their defence to become the real strong men of the team. It will be probably be the deciding factor on whether or not Chelsea can realise owner Roman Abramovich's pursuit of a first Champions League trophy on Di Matteo's watch. Abramovich prefers attacking flurries, but the end justifies the means if Chelsea can quell a side full of Teutonic goodness.
This colossal occasion is a huge contrast from where Di Matteo was three years ago when he coached MK Dons to the League One play-offs only to lose narrowly in the semi-finals to Scunthorpe United on penalties. Armed with his coaching badges, West Bromwich Albion hired him in 2009. He responded by winning promotion behind Newcastle United to the Premier League.
He was sacked and replaced by Roy Hodgson after overseeing a run of one win in 10 games last year. He was rejected for the Birmingham position before being brought back to Chelsea under Andre Villas-Boas's umbrella. The rest is history.
It was interesting hearing Frank Sinclair offering the opinion a few weeks ago that perhaps Di Matteo the player was not the outstanding favourite to forge a coaching career when they were team-mates in a squad laced with more vocal characters such as Dennis Wise and Frank Leboeuf.
"I never realised that in order to become a jockey you have to have been a horse first," said Sacchi famously.
With his head shorn, Di Matteo perhaps cuts a similar figure to Sacchi these days. Di Matteo is well mannered, straight-talking and a good conversationalist. Chelsea have a thinking man in their corner in Munich.
In four years he has gone from pro-celebrity golf to the cusp of becoming a Champions League winning-coach. Di Matteo has came a long way from Abu Dhabi to the Allianz Arena. We watched Martin Kaymer win a golf tournament that weekend, but further German tomfoolery is not on the mind of the visiting manager on this particular one.
Logic may suggest otherwise, but 'Dima' can take one more unlikely step on the road to the palace of wisdom.