Brendan Rodgers has been in a Premier League title race with Liverpool, won the lot in Scotland with Celtic, and tasted Wembley success in the Championship play-off final with Swansea in 2011.
However, a major English trophy is currently missing from his CV - and he has the chance to address that on Saturday, when his Leicester side take on Chelsea in the FA Cup final.
Rodgers has had a remarkable impact at Leicester, with the Foxes on course for a top-four finish this season after frustratingly slipping out of the Champions League qualifying places last season.
However, a piece of silverware would be a tangible recognition of the improvements he's made at the club.
Speaking on the Pitch to Post Preview Podcast ahead of the final, Sky Sports News reporter Paul Gilmour said victory for Rodgers over Chelsea - the club where he was once youth and reserve team boss - would be a significant step up, in terms of his standing as a manager.
"It would propel him to another level," said Gilmour.
"He's already well thought of, everybody knows what type of manager he is. I get the impression he's highly ambitious as well.
"It wouldn't surprise me if he managed Chelsea at some point in the future because of his links to Chelsea and I wonder if he has some unfinished business there at some point in his career. But for the time being, at Leicester, he's made them so consistent.
"You can see the work he's done at Liverpool, Celtic and Leicester, he's proven himself to be a very talented manager. A player's manager. Players love him. I've spoken to quite a few Leicester players, and Jonny Evans more than anybody, and Jonny raves about him.
"But if he starts to add trophies to that it will just propel him to that next level.
"It's no surprise to me to hear Tottenham have been monitoring him over the years and keeping an eye on him. That's the kind of calibre of manager he is.
"He's going to be at the very top level of the game and he deserves to manage in the Champions League. If Leicester can hold on and get that top-four place, he'll be right at home in that competition next season."
Will Iheanacho be Leicester's hero?
If Rodgers and Leicester are to pull of the FA Cup win - the first in the Foxes' history - they'll need to find a way through Chelsea's mean defence. Under Thomas Tuchel, the Blues have kept 19 clean sheets in 26 games.
However, while Jamie Vardy (two goals in his last 24 games) has struggled to re-find his goal-scoring form since having a hernia operation earlier this year, Kelechi Iheancho has stepped up.
Leicester's Nigerian striker has hit 15 goals in his last 17 games and has an outstanding record in FA Cup ties, finding the net 14 times in his last 19 appearances in the competition.
Sky Sports football writer Ron Walker says sustaining that output will be the next challenge for Iheanacho, 24, as he looks to establish his reputation, but believes Leicester have the tools at their disposal to trouble Chelsea.
"Iheanacho has always looked like he had something about him," Walker told the Pitch to Post Preview Podcast. "Even when he was at Man City and he was very raw. There was a reason he was on the fringes there and sometimes you just need something to fall for you and then it goes like that.
"It will be interesting to see whether this is a purple patch or if he can keep these sort of numbers up to be a first-choice striker for a team in the Champions League places.
"But Rodgers, to a certain extent, would have been sat quite happily watching Arsenal against Chelsea. I know Chelsea made a lot of changes but Arsenal were happy to sit back, soak up pressure and try - although not massively succeed - to hit Chelsea on the break.
"I know Rodgers has made Leicester into a team more comfortable on the ball but the way they won the Premier League was hitting teams on the break. I know Vardy has changed his game a little bit and he's becoming more of the man to play alongside Iheanacho at the moment but they have plenty of pace in the team.
"Chelsea have only scored more than two goals in one game in the entire time Tuchel has been there. They're just not that prolific, so if you can frustrate them, with the pace, trickery and guile Leicester have got on the break, they're always going to get chances."
Kante the key
As for Chelsea, the return of N'Golo Kante to the side could be the key factor, says Gilmour. The French World Cup winner has been in impressive form in recent weeks but was left out of the squad against Arsenal on Wednesday night to rest an Achilles problem.
If he is fit to play, he could be the difference, says the Sky Sports News reporter.
"The midfield battle should be really interesting because if Kante is OK - and by all accounts it seems it was precautionary resting on Wednesday against Arsenal with his Achilles - he has been back to his sensational best," said Gilmour.
"Leicester know exactly what he's about. But that midfield battle could be crucial. When James Maddison is on the top of his game he's a massive threat but we just haven't seen it enough from him since he got back from injury. Then you bring Youri Tielemans into that as well, against Jorginho and Kante, who are probably going to be the 'double-six' for Tuchel.
"I see that area of the field being a key part of the Cup final - and if Kante plays to the level he's played at recently, he's enough to make a difference."
Pitch to Post Preview - FA Cup Final special: Will Chelsea or Leicester lift the trophy?
In a special episode of the Pitch to Post Preview Podcast we look ahead to this Saturday's FA Cup Final at Wembley, where Chelsea and Leicester will battle for the trophy in front of over 20,000 fans.
Peter Smith is joined by Sky Sports News reporter Paul Gilmour and Sky Sports football writer Ron Walker to assess both sides on the back of their midweek results, the key areas which will decide the contest, and how the game will play out.
They also discuss what impact FA Cup glory would have on Brendan Rodgers' managerial career, the importance of Jonny Evans at the heart of the Leicester defence, and why former Foxes star N'Golo Kante could be the decisive player on the pitch this weekend for Chelsea.
Listen to the Sky Sports Pitch to Post Podcast on: Spotify | Apple | Castbox