6. Martin Jol
When Jol took over early in the 2004 season, little was known and even less was expected of the Dutchman. He had initially been appointed as First Assistant Coach to Santini, but only after 12 games, he was appointed the head coach.
Jol’s personality quickly endeared him to Spurs supporters – and more importantly, so did the team’s improvement under his stewardship. In his first full season, the club finished fifth. Jol did what no manager had done since Keith Burkinshaw and kept Spurs in the top five of the table in consecutive seasons.
The next summer, he signed Gareth Bale, convincing the Southampton youngster and his parents that Spurs would be a better place for his development than Manchester United. Given the impact that Bale would leave on the club, that signing alone is almost worthy of a place on this list of best Tottenham managers ever, but he’s done much more than that.
5. Harry Redknapp
Harry Redknapp got the best out of the Spurs squad during his near-four seasons in charge. Taking over Spurs in 2008, which had suffered the club’s worst-ever start to a season, Redknapp steered them to eighth and the League Cup final. He also led to fourth place next season, thus qualifying for UCL football.
There was also that memorable run to the Champions League quarter-finals in 2011. Football is as much about memories as it is results, and Redknapp created plenty of those.
Despite leading Tottenham to their second fourth-place finish in three years and missing out on Champions League qualification only due to Chelsea winning the competition, Redknapp was sacked by Tottenham on 13 June 2012.
4. Mauricio Pochettino
Pochettino was appointed head coach of Tottenham Hotspur in May 2014, becoming their tenth manager over a 12-year span. Tottenham played an attractive brand of football under the Argentine.
In the domestic league, his first season was generally successful, ending in a fifth-place finish and the conversion of several young academy players into regular first-team players, he put one of those graduates, Harry Kane, as starting striker at the expense of Spanish international Roberto Soldado, a gamble which paid off.
Under Pochettino, the transformation of Spurs was massive. He guided Spurs to Champions League football and also reached the final of the UCL in 2019. Pochettino was dismissed by Tottenham Hotspur in Nov 2019, with the side placed 14th in the Premier League table. Club chairman Daniel Levy cited “extremely disappointing” domestic results as the reason behind the dismissal.