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.
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"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."
Jones Knows' prediction
Those that like backing cards have endured a frustrating period behind closed doors as referees have become more lenient without the pressure of a crowd roaring them on to delve into their pockets. Michael Oliver has got the nod for this one and he will undertaking his duties with 20,000 fans inside Wembley. The added edge of an atmosphere in a one-off game environment where cynical fouls are more likely to be seen, should result in a card friendly game.
And I want to back Wilfred Ndidi to get one at 3/1 with Sky Bet. He's having another magnificent season in the engine room but he's being asked to play with more dynamism in a midfield two and the fouls have been racking up. Since the start of April, no player has made more fouls in the Premier League than Ndidi (19), picking up two bookings along the way.
Furthermore, in what I would define as "elite encounters", Chelsea's style of breaking through their midfield into their front three is causing opposition players to make fouls. In the two legs vs Real Madrid in the Champions League, the Spanish side picked up nine bookings in total whilst Manchester City were carded five times across their meetings recently and Porto seven times. Cards are on the menu in a Chelsea win.
BETTING ANGLE: Wilfred Ndidi to be carded (3/1 with Sky Bet)
Chelsea boast a fully-fit squad for Saturday's FA Cup final against Leicester.
Mateo Kovacic has shaken off a hamstring injury and N'Golo Kante is back after Achilles tendon pain. Andreas Christensen has also beaten a leg tendon issue.
Jonny Evans faces a race to be fit for the Foxes' first FA Cup final since 1969.
The defender has been nursing a heel problem which has forced him to miss the last two games and he will be given until the last minute to prove his fitness.
James Justin and Harvey Barnes (both knee) are sidelined while Cengiz Under has been nursing a hip problem and Wes Morgan is out with a back issue.
- This will be the 140th FA Cup final, with Chelsea and Leicester becoming the 117th different pairing in the competition's showcase. Manchester City's 6-0 demolition of Watford in 2019 was the last time two sides met in the final for the first time.
- This season's FA Cup final will take place before the end of the Premier League season. The last time this happened came back in 2012-13, when underdogs Wigan beat Manchester City 1-0 to lift the trophy.
- Chelsea will be appearing in their 15th FA Cup final, with only Arsenal (21) and Manchester United (20) reaching the competition's showcase on more occasions. Indeed, only the Gunners (14) and the Red Devils (12) have won the trophy on more occasions than Chelsea (8).
- This will be Leicester City's fifth appearance in an FA Cup final and their first since 1969. The Foxes have lost all four previous finals, the most appearances a side has made in the competition's showcase without ever winning the trophy.
- Chelsea have reached the FA Cup final in four of the last five seasons (W1 L2), with the Blues finishing runners up in last season's competition to Arsenal. The last side to lose the FA Cup final in consecutive seasons was Newcastle in 1998 and 1999.
- Including replays, Chelsea have only played more FA Cup matches without ever losing against Hull City (11) than against Leicester (9 - W7 D2), progressing from each of their previous seven ties against the Foxes in the competition.
- Leicester City will be appearing in the final of a major cup competition for the first time since 2000, beating Tranmere 2-1 at Wembley in the League Cup final, courtesy of a brace from captain Matt Elliott.
- Chelsea have reached the final of a major domestic/European cup competition in five consecutive seasons for the first time in the club's history (2017 FA Cup final, 2018 FA Cup final, 2019 League Cup and Europa League final, 2020 FA Cup final and 2021 FA Cup and Champions League final).
- Leicester City have won just four of their 15 games played at Wembley stadium (D1 L10). Following their victory against Southampton in the semi-final, the Foxes will be aiming to win back-to-back matches at this venue for just the second time, previously doing so when winning the 1994 and 1996 second tier play off finals.
- Chelsea have lost four of their last seven trips to Wembley (W2 D1), as many defeats as in their previous 17 visits to this ground (W11 D2).
- Leicester City boss Brendan Rodgers - who won the Scottish FA Cup with Celtic in 2017 & 2018 - could become the first manager to win both the English and Scottish FA Cup since Sir Alex Ferguson (four Scottish FA Cup titles with Aberdeen and five English FA Cup titles with Man Utd).
- Chelsea boss Thomas Tuchel will become the first ever German manager to lead his side out for an English FA Cup final, with the Blues still yet to concede a goal under him in this season's competition.
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.