Mourinho led his team to 25 trophies over the course of his career.
This summer, the Portuguese were named to his ninth club, Roma in Italy, and his side's match against Sassuolo on Sunday will be the 1,000th game of his coaching career!
Mourinho has an overall win rate of 63.76%, winning 637 of his 999 games to date, with 204 draws and 158 defeats.
Mourinho has experienced a lot of ups and downs in his long career in football, signing a lot of players in the last 20 years, let's take a look at his best signings and worst signings in all these years.
Mourinho's best signing
5. Snyder (Real Madrid transfer to Inter, 2009, £13.3 million)
The Dutch midfield master played an important role in Inter's brilliant treble in 2009-10.
After leaving Real Madrid, Sneijder became the most influential player in the world that season, not only leading Inter to trebles, but also leading the Netherlands to the World Cup final that summer.
However, in the end, the Barcelona trio Messi, Iniesta and Xavi finished on the podium of the Annual Ballon d'Or, but Sneijder unfortunately did not finish on the podium.
4. Diego Costa (Atletico moved to Chelsea in 2014, £32 million)
The Brazilian-born striker has established himself as the world's top striker at Atletico Madrid before moving to the Blues – he has won titles in La Liga and the Champions League.
Costa helped Jose Mourinho's Chelsea win the Premier League and League Cup in his first season and played a key role in three seasons at Stamford Bridge, including winning the title under Conte in 2016/17.
3. Modric (Tottenham Hotspur moved to Real Madrid in 2012, £30 million)
As time went on, Croatian midfielder Modric was in better shape.
Although Modric did not create his best form under Mourinho's rule, in fact, his signing was widely ridiculed by the anti-Madrid media in the Spanish media, but then Modric established himself as a world-class player.
A key member of four Champions Leagues, Modric led Croatia to the World Cup final in 2018, when he won the Ballon d'Or.
2. Ashley Cole (Arsenal moved to Chelsea in 2006, £5 million + Willian Galla)
Cole is widely regarded as the greatest left-back of his generation, and in an exchange deal he moved from north London to west London.
Kerr's highest level of defensive ability and excellent physical fitness was not fully appreciated until after his retirement, a signing that really laid the foundation for Chelsea's success in the years to come.
1. Drogba (Marseille moved to Chelsea in 2004, £24 million)
The greatest and most influential player of Mourinho's coaching career, Drogba scored 157 goals for Chelsea in 341 games, including an equaliser in the 2012 Champions League final against Bayern Munich.
As an icon of Stamford Bridge, Drogba's influence on and off the pitch is unquestionable, with his winning spirit and never-say-die attitude echoing Mourinho's attitude on the pitch.
He won the Champions League four times, as well as several domestic trophies.
Mourinho's worst signing
5. Kejman (Eindhoven moved to Chelsea in 2004, £5.3 million)
Serbian striker Kegerman joined Chelsea in 2004, before scoring 38 goals for Eindhoven.
But by Chelsea, he had scored just four goals in 25 games at the club and after 12 months at the club, he moved to Atletico Madrid. Kegerman's signing, while a good choice, is definitely not a successful signing.
4. Quaresma (Porto moved to Inter Milan in 2008, £22.1 million)
Quaresma had a difficult time at Inter. There is no doubt that Quaresma has super personal ability and outstanding performance ability, but he has never found his best form at Inter.
The man from Porto never really entered the club after Mourinho joined the club, scoring just one goal in the club's 32 appearances before being loaned to Chelsea and subsequently sold to Besiktas.
3. Cuadrado (Fiorentina moved to Chelsea in 2015, £23.3 million)
The winger started for Fiorentina after playing for Colombia at the 2014 World Cup, but has never replicated his previous form at Stamford Bridge after moving to Stamford Bridge in January 2015.
After a tough start for the winger, Mourinho said confidently: "He needs time, I know Italy, I know the difference between Italy and England. His training, his development, his experience everything is in Italy. Stability, time, integration, I think we'll see the best players next year. ”
Before joining Juventus, he had only played 15 games for the Blues.
2. Shevchenko (AC Milan moved to Chelsea in 2006, £30 million)
The legendary Ukrainian striker joined Premier League champions Chelsea from Milan in 2006 and his arrival is believed to re-establish their supremacy at home.
However, Shevchenko's arrival has had a negative impact, he is not suitable for the Blues and it is difficult to find his form in the club.
With 23 goals in 76 games, it's far from a disaster, but a goalscorer like him should have a bigger impact and in his form it's impossible to win the league title at the Blues.
1. Alexis Sanchez (Arsenal transferred to Manchester United in 2018, exchange with Mkhitaryan)
In January 2018, United beat rivals Manchester City to move from Arsenal to Alex Sánchez, becoming the highest-paid player in the Premier League.
It was an unmitigated disaster, with Sanchez scoring just five goals for United and being loaned to Inter in the summer of 2019 before moving on as a free agent the following year, united desperately wanted to sell him because of his outrageously high salary.
It was the worst transfer of Mourinho's career and quite possibly the worst in United's history.