There are only four managers in this season’s Champions League who have won the trophy: Jose Mourinho, Pep Guardiola, Carlo Ancelotti and Rafa Benitez.
The Spaniard is considered one of the dark horses to lift it again this season, thanks to his competition nous, and his cracking start to life at swashbuckling Napoli.
He takes the Serie A high flyers to London tonight, where they will contest an intriguing battle with Premier League leaders Arsenal.
Rafa and Gunners manager Arsene Wenger enjoy a cordial relationship, and the Frenchman admits he covets the European title his friend won when manager at Liverpool.
Confidence is currently flowing through the Gunners’ veins, and Wenger says he hopes this season he can fill the glaring hole on his CV that should read: European trophy.
"It is something I miss," he said ahead of what should be a cracking game, in reference to his failure to win at the highest European level.
"I will try to fight very hard to fill my CV with that.
“But you play against Barcelona, Bayern, Real Madrid – every year they are there with a chance.
“Every year you always think: 'Let's do it', and one year it will go for you. Let's hope it will be this year."
Of his adversary tonight, Wenger added: "I'm not surprised Rafa is doing well.
"Maybe his first experience in Italy [at Inter Milan] he took a team who had been at a high and they were just over the hill, so that was a bit of a gamble. Napoli are on the way up. He can give them more experience and quality."
Benitez meanwhile, is loving life at Napoli, where he says he has found a Liverpool-like approach to football.
"It's a nice place, nice fans with a lot of commitment. It's very similar to Liverpool in the passion for the team and the enjoyment of football. You see it everywhere. That's why it has been easy for me," he said.
He also praised Wenger freely, but warned him friendship will count for nothing when two in-form teams take to the pitch to do battle tonight.
"I think Arsene Wenger is the best coach in the Premier League," he said.
"He's a great manager, great person, always top-four doing a great job. Hopefully he can win [the Champions League]. But another year. Not this one."
As usual in the Champions League, there are a host of mouth-watering ties to savour tonight. But Arsenal v Napoli may just be the game to watch.