Thierry Henry spent part of a season at Juventus between his times at Monaco and Arsenal
On Wednesday, an exciting Monaco side go head to head with a imposing Juventus in the first leg of their Champions League semi final tie.
It comes almost 20 seasons since both clubs met at the same stage of the competition with Juve reaching the 1997-98 final after overcoming Monaco 6-4 on aggregate.
On the Monaco team that day were two future Juventus players - former France World Cup winners Thierry Henry and David Trezeguet.
The latter would go on to enjoy a successful stint in Turin for future Arsenal legend Henry it would prove a year to forget. And he's not the only forward to have moved to Serie A briefly to face their notoriously tough defences and then reignited their careers elsewhere.
The scorer of 175 Premier League goals for Arsenal, Henry arrived in London a little under the radar after a underwhelming spell at Juventus. Indeed, Juventus had outbid Arsenal in order to secure his signature, even though it would eventually be the Gunners who would benefit greatly.
Having won the World Cup in July 1998, six months later he moved to Italy but for a player who would later go on to become a feared striker, Henry was often played as a winger in Turin.
Just three goals in 19 appearances would follow in all competitions as the then 22 year old struggled to make an impact.
Henry detailed the reasons for his struggles in an interview with Reuters, saying, "When I arrived the team was ninth in the league and we finished sixth, there were a lot of problems in the club. Lippi wanted to play me as a centre-forward, I remember the first two games when I arrived he put me on the bench but everytime I came on it was as a centre-forward. Then Ancelotti arrived and I played the remainder of the season on the left and at the very beginning I kind of struggled, I had to get used to the pace of the league, I had just arrived and a new position – we were playing 3-5-2 and so I had to cover the whole left side."
Just over six months after arriving, Henry was reunited with Wenger at Arsenal and the rest as they say is history.
For a time, the man who scored the winner for Ajax in the 1995 UEFA Champions League final was the Netherlands' record goalscorer at international level.
Shortly after that triumph, that young Ajax team was torn apart by other clubs with many players heading to Serie A.
Kluivert was one of them, joining AC Milan in the summer of 1997 during one of their worst seasons. They would finish the 1997-98 season down in 10th and on an individual level Kluivert, who was just 21, would score just nine times in 33 fixtures in all competitions, including just six in Serie A.
At the end of the season, he was off to Barcelona to be reunited with his former Ajax boss Louis van Gaal where he is far more fondly remembered as a forward.
Last week, the Ireland record goalscorer was singing the praises of his former Inter Milan team-mate and room-mate Clarence Seedorf.
Keane's Inter career was very brief from the summer of 2000 before moving to Leeds United.
Why did it not go as well as it could have? Richard Hall of The Gentleman Ultra once explained the Keane-Inter story on Team 33, which you can listen to below:
Keane of course would later bang in the goals for club but more significantly for country after his brief time in the blue and black half of Milan.
Another difficult Serie A career at Inter that we examined very recently was that of Dennis Bergkamp who was derided by the local media during two difficult years at the club after signing from Ajax
A future Arsenal legend - despite a slow start - Richard Hall also detailed the reasons for Bergkamp's struggle in the podcast below: