Before taking charge of Chelsea, Di Matteo's managerial résumé had not been particularly impressive.
In 2008, he managed Milton Keynes in English League One. His team finished third that season, but lost to their opponents in the English Championship promotion playoffs and missed their chance to move up.
Although he had failed to lead Milton Keynes into the English Championship, Di Matteo's solid performance over the season earned him the opportunity to manage English Championship side West Bromwich, a famous yo-yo club in the Premier League.
A so-called yo-yo club was one that frequently moved back and forth between the Premier League and the English Championship.
In his first season as West Bromwich's manager, Di Matteo successfully led the team into the Premier League. That earned him plenty of praise. Even after promotion, despite the painful memory of losing 6–0 away to Chelsea in the very first round, the team quickly recovered. At one point, they climbed to sixth in the Premier League, defeated Arsenal, and drew away to Manchester United. Their performance was truly outstanding.
During that period, Di Matteo's reputation soared, attracting attention from across the United Kingdom and even the European football world.
But the good times did not last. West Bromwich's relatively open style of play, combined with a severely inadequate squad, left the team lacking stamina and depth. Di Matteo was dismissed in February 2011.
Last summer, after failing to secure the Birmingham job, Di Matteo accepted Boas's invitation to become the Portuguese manager's chief assistant at Chelsea, officially returning to Stamford Bridge.
No one had expected that Di Matteo, who had not even won Birmingham's favor, would replace Boas just six months later after Boas was fired, becoming Chelsea's manager and leading the team into the Champions League final.
Fate was truly impossible to