6. Harry Redknapp
In October 2008, following the sacking of Juande Ramos by Tottenham Hotspur, the club announced that Redknapp had agreed to take over as the new manager at Spurs, the club where he began his playing career.
Spurs had secured only two points from the first eight games of the season prior to Redknapp’s arrival and lay bottom of the league, but in his first two weeks in charge he took the club out of the relegation zone, winning ten out of the twelve points available with wins against Bolton Wanderers, Liverpool and Manchester City and a remarkable 4–4 draw against North London rivals Arsenal.
In March 2009, Redknapp led Spurs to the League Cup final, which they lost on penalties to Manchester United. Spurs eventually finished in eighth position with 51 points, narrowly missing out on a Europa League place.
In 2009–10, his first full campaign with the club, Redknapp guided Spurs to their most successful Premier League season to date. Beginning with four consecutive wins,Spurs went on to finish in fourth place with 70 points, thus gaining the chance to qualify for the Champions League. As a result of his efforts he won the Premier League Manager of the Year award, only the second manager to do so in a season when his side did not win the title.
Despite leading Tottenham to their second fourth-placed 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.
5. Martin Jol
When Jol took over early in the 2004 season, little was known and even less was expected of the Dutchman. Tottenham had been mired in mediocrity for a decade under the rudderless guidance of Alan Sugar, and Jol’s team was lacking in real quality and had not finished higher than eighth since 1996.
In Jol’s first full season, he came within a single match of beating Arsenal to fourth place and a Champions League appearance. The story of that day against West Ham is well known to Spurs fans, but the fact that he took that team so close is an achievement in itself.
Despite falling at the final hurdle, Jol took Spurs into Europe, signed Dimitar Berbatov and finished fifth again.
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, but Jol laid the groundwork for Harry Redknapp and the era of sustained competitiveness that Tottenham still enjoy.
4. Mauricio Pochettino
Pochettino was appointed head coach of Tottenham Hotspur in May 2014, becoming their tenth manager over a 12-year span.
In the domestic league, his first season was generally successful, ending in a fifth-placed 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 citing “extremely disappointing” domestic results as the reason behind the dismissal.