In the shadows of his 40th birthday, Andre Villas-Boas is on the cusp of the biggest Asian club final of all.
His first season in China could finish with a flourish, as he more than capably fills the sizeable shoes of Sven-Goran Eriksson.
Shanghai SIPG will take a 1-1 scoreline to Saitama Stadium next month after a tense AFC Champions League semi-final against Urawa Red Diamonds on Wednesday night.
The Japanese side will be difficult to overcome at home, but with the likes of Oscar, Elkeson and Hulk, who scored a spectacular goal in the first leg, the Chinese giants will fancy their chances.
The second leg will be held on Oct. 18, the day after Villas-Boas turns 40, and almost four years after he turned his back on the Premier League.
His stints in charge of Chelsea and Tottenham Hotspur, lasting a combined 26 months, were not successful, although he might point to a respectable 55-percent winning rate at White Hart Lane across two seasons until December 2013.
Since then, the Portuguese coach has steadily rebuilt his reputation -- first at Zenit Saint Petersburg where he won three major trophies, and now at Shanghai SIPG, despite the odd, colourful controversy off the field.
Villas-Boas was fortunate to escape suspension from Wednesday night's match after claiming that Chinese Super League (CSL) rivals Guangzhou Evergrande had deliberately engineered car accidents to disrupt SIPG's route to the stadium for the away portion of their ACL quarter-final on Sept 12.
SIPG almost blew a 4-0 first-leg lead against the CSL champions, squeaking through on penalties after a 5-1 away defeat in one of the wildest games ever seen on the Asian stage.
Earlier in the season, Villas-Boas served a two-game CSL ban after using social media to show personal support for Oscar after the ex-Chelsea midfielder received an eight-match suspension for his part in a mass brawl in June against Guangzhou R&F.
And as recently as last Friday, he was dispatched to the stands for questioning refereeing decisions in a 1-0 win over Beijing Guoan.
Given his eventful first year in China, it might be a stretch to say that Villas-Boas has developed a wisdom and prudence to go along with his renowned energy and enthusiasm.
The years of working along Jose Mourinho at Porto, Chelsea and Inter Milan, undoubtedly influenced the kind of sometimes-volatile manager that Villas-Boas has become.
But, with almost a decade of being a head coach at the top level, Villas-Boas now has a greater assuredness and depth of experience to call on.
At Chelsea, he took over in 2011 when he was still shy of his 34th birthday. At the time, he was only eight months older than Frank Lampard, with whom he clashed. He would later admit that it was "too much too soon" because he wasn't flexible enough in his approach.
In Shanghai, Villas-Boas lives in the upmarket Pudong district, and has impressed the fans with the improvements he has made to the side since the departure of Eriksson after two seasons last November.
Not only did he bring his former players Oscar and Ricardo Carvalho to Shanghai, he has helped developed several local youngsters, including striker Li Shenglong and winger Lin Chuangyi.
SIPG have played some sparkling football in 2017 -- their 62 goals is the best in the CSL -- but defensively, they have made strides as well. SIPG boast the joint second-stingiest defence, conceding only 29 times in 26 league matches.
Stopping Guangzhou Evergrande from winning a seventh consecutive CSL title may be beyond Villas-Boas' grasp, with Luiz Felipe Scolari's side holding a four-point lead at the top of the table, with only four games remaining.
But to guide Shanghai SIPG to their first Asian trophy would be an incredible achievement for a man who became European football's youngest champion coach at the age of just 33 when Porto claimed Uefa Europa League glory in Dublin in 2011.
That would prove a point to the sceptics from his Premier League days who may have once thought of AVB as a poor man's Mourinho, even though he's repeatedly stated that he has no desire to return to England.
Jason Dasey is Singapore-based senior editor of football website ESPN FC. Twitter: @JasonDasey