Andrea Pirlo takes his first managerial steps in the Champions League at Dynamo Kiev on Tuesday, a game which pits the fledgling Juventus coach against his vastly experienced former mentor Mircea Lucescu.
Lucescu, 75, and 41-year-old Pirlo have both taken over their respective clubs this season.
But while Italy footballing legend Pirlo never coached before stepping up at his former club, Lucescu has over four decades experience throughout Europe.
And it was the former Romanian international who gave a 16-year-old Pirlo his first Serie A start in the Italian's hometown club Brescia 25 years ago.
The much-travelled Lucescu also later coached Pirlo at Inter Milan in 1998.
For Lucescu, who won six league titles as a player with Dinamo Bucharest in the 1960s and 1970s, seeing Pirlo on the opposition bench comes as no surprise.
"I was always convinced he would become a coach," said Lucescu.
"I thought it about Andrea, and also Diego Simeone, who was one of my players at Pisa.
"Pirlo had a different personality than 'Cholo' (Simeone) but he was just as charismatic and with a lot of character.
"Above all, he never came on the pitch to do nothing, he was decisive.
"As well as being a creative player, he was someone who organised everything, which is yet another skill."
Whether he can follow former players Pep Guardiola and Zinedine Zidane's managerial success remains to be seen.
"It's possible, I hope he does," the Romanian told Turin daily Tuttosport.
"But a coach needs at least six months to stamp his mark on a team."
Pirlo took over the reigning nine-time Serie A champions after Maurizo Sarri was sacked following Juventus' Champions League last 16 exit to Lyon.
Juve hope Pirlo, who won a World Cup, two Champions Leagues and six Italian league titles as a player, can transmit his vision of the game.
The team are chasing a third Champions League title after 1985 and 1996, with seven runners-up finishing including in 2015 and 2017.
- 'No miracles' -
But for Pirlo, his Juventus are "under construction, a young team who need to gain experience".
A season-opening 3-0 win over Sampdoria was followed by draws at AS Roma (2-2) and promoted Crotone (1-1), with two red cards in as many games.
To complicate the task, Cristiano Ronaldo is quarantined because of coronavirus, and will miss the Kiev trip and possibly the game against Barcelona in Turin.
As models Pirlo cites the Barcelona teams of Guardiola and Johan Cruyff, Louis van Gaal's Ajax, Carlo Ancelotti's AC Milan and Antonio Conte's Juventus.
But first up are Lucescu's Ukrainian league runners-up.
"It's a competition that I'm accustomed to," said Lucescu whose appointment as Kiev boss had sparked an uproar after his successful 12-year spell in charge of bitter rivals Shakhtar Donetsk, where he won the 2009 UEFA Cup.
"It's a competition that I'm accustomed to. I've been involved in more than 130 games.
"The Champions League anthem is like your national anthem."
Lucescu's Dynamo are also "a very young squad".
"My aim is to build this team," he said.
"It's not possible in football to start and get results straight away. There are no miracles in football."
Over his 40-year career, Lucescu has coached the Romanian and Turkish national teams as well as clubs in Romania, Italy, Turkey, Ukraine and Russia.
"I find motivation in my passion for football," he told UEFA.com.
"I tried to stop last year, because I've worked for 50 years without a break, but it was impossible.
"I wanted to come back, there was so much I could still give to football, especially to young players.
"So, I came back and I feel good being back at work."