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Mauricio Pochettino was loved by many during his time at Tottenham and took his side to the Champions League final in 2019.
Despite this, he wasn't able to solve Spurs' now almost 14-year trophy drought, which will continue for another season after their exit from the FA Cup on Tuesday.
The Lilywhites travelled to the Riverside Stadium but lost 1-0 to Middlesbrough, in a game which was there for the taking, but Tottenham failed to take their chances.
The fifth round tie was Spurs' last chance at getting silverware this season, but now that hope is over for another year.
Whilst the Argentine was in charge, Tottenham finished in the top four for four seasons in a row, reaching the final of the Champions League before Pochettino's departure.
Since then, no manager has quite found the same success and the last two seasons have found Spurs falling below that desired spot in the Premier League table.
Antonio Conte's arrival has installed some hope back into the club and with his winning history at Chelsea, Juventus and Inter Milan, there is no better man to take the north London side back into the top European competition.
However, the Italian also needs a quality squad of players to do so and with four first team