Frank Lampard and Antonio Conte, both giants of the footballing world, are set to collide on Monday when Tottenham host Everton.
Lampard is 19 years younger than the Italian, so there's no doubt who has had the better success in the dugout, but as players, both Lampard and Conte picked up trophies at the highest level.
Conte won five Serie A titles with Juventus, as well as two European trophies, but like Lampard, all of his success came at one club.
Lampard made a name for himself at Chelsea, and even though he played for both West Ham and Manchester City, it was his career at Stamford Bridge that will be remembered the most.
Lampard remains Chelsea's all-time record goalscorer, some achievement for a midfielder, but he also won three Premier League titles, four FA Cups, the Europa League and Champions League.
As a coach, Lampard is only just getting started. Still, for all of Conte's experience, he is having the same issues as the former England international.
Both men will go head-to-head on Monday night as Spurs and Everton go toe-to-toe in north London.
Tottenham are priced at 8/15 to pick up all three points against 5/1 Everton, while the draw is available at 3/1.
Questions are being asked of both coaches at present, and there's every chance one of them may move on in the summer if things do not improve.
As a player, Lampard achieved pretty much everything he wanted. The only downside came on the international stage, as he was part of the golden generation that failed to impress under numerous managers.
As a coach himself, Lampard showed signs of potential at Derby County, but after failing to get the Rams promoted, he jumped at the chance to coach Chelsea.
Lampard has since admitted that move came too soon in his career, but he was given a second chance by Everton in January.
The Toffees, 7/2 to be relegated, decided to part company with Rafael Benitez after a dire run of results, but things have not taken a dramatic twist just yet.
Lampard joined on transfer deadline day and immediately sanctioned moves for Donny van de Beek and Dele Alli.
While Lampard managed to get his team to beat Leeds United, he has lost every other league game so far.
Everton have lost seven of their previous nine games in the top flight, and that run of form has seen them drop into the relegation fight.
Lampard's men are just one point above the drop zone, but they do have two games in hand on 18th-placed Burnley and three over Leeds, who sit above them.
As a coach, Conte demands the very best from his players due to his all-action style.
His methods have worked in the past, with Juventus winning three successive league titles under his stewardship.
At Chelsea, he transformed them in no time, helping them win the Premier League and FA Cup in successive campaigns.
At Inter, he had a similar effect, winning the Serie A title before moving onto pastures new.
Conte rejected the chance to join Spurs during their first approach, but he eventually folded and agreed to replace Nuno Espirito Santo in November.
His tenure has been full of drama, and it nearly came to a head at the end of last month.
Following their 1-0 defeat to Burnley, Conte offered to walk away from his role, and it seems like his entire spell at Spurs is ready to end in disaster at any minute.
Fortunately for Conte, his team seem to be able to pick up results on a sporadic basis, but after beating Leeds United 4-0 last weekend, they were brought back down to earth by Middlesbrough in the FA Cup.
For now, it seems like Conte has had the biggest impact, mainly because Spurs are still in with a chance of finishing in the top four.
Tottenham, 4/1 to finish in the top four, have two games in hand over Manchester United, who currently occupy fourth spot.
Lampard's start to life at Goodison Park has been tough, and their upcoming fixture list suggests his abilities will be tested to their max.
Everton have never been relegated from the Premier League, but if they can avoid the drop, Lampard will have proven himself at the highest level.
For the first time in his career, Lampard is involved in a relegation scrap, and that lack of experience could be telling come the end of the season.
Should Everton get the job done, then Lampard can look forward to next season with optimism.
Neither he nor Conte look comfortable in their current surroundings, but for now, the Italian looks to have more of a grip on his current predicament.