Most Successful Tottenham Managers Ever

At the time of writing, Tottenham Hotspur manager Antonio Conte appears not to want to commit to the club beyond the end of the current season (when his contract expires). It seems the feeling may well be mutual so more than likely we will see a new boss in charge next term. There are plenty of Spurs fans who wouldn’t be too upset to see the back of the Italian, despite his pedigree. Like most who’ve occupied the Tottenham dugout, Conte has failed to bring any silverware to the club.

But let’s put Conte aside and take a look back at the managers who did win things with Spurs. Before we go through the managers themselves, we’ll summarise the honours Tottenham have won over the years.

Tottenham Honours

Competition Number Seasons
First Division* Title 2 1950/51, 1960/61
Second Division** Title 2 1919/20, 1949/50
FA Cup 8 1900/01, 1920/21, 1960/61, 1966/67, 1980/81, 1981/82, 1990/91
League Cup 4 1970/71, 1972/73, 1998/99, 2007/08
Charity Shield/Community Shield 7 1921, 1951, 1961, 1962, 1967, 1981, 1991
UEFA Cup Winners’ Cup 1 1962/63
UEFA Cup 2 1971/72, 1983/84

*The First Division was the top tier of English football on the two occasions Spurs won it. **The Second Division was the second tier of English football at the time.

For a club still considered one of the Big Six, it is interesting that Spurs haven’t won a major tournament since the 2007/08 season, and that was only the League Cup! In addition, they haven’t won the FA Cup since 1991 (when Paul Gascoigne and Gary Lineker played for the club). And we have to go even further back to the 1960/61 season for the last time they won the top-flight title (though, to be fair, they did achieve the league and cup double that season). Indeed it’s the manager who guided Tottenham to their first (and so far only) double who sits at the top of our list.

Bill Nicholson, 1958 to 1974

For many Spurs fans, there is no debate about the greatest-ever manager of Tottenham Hotspur: it is Bill Nicholson. His trophy haul dwarfs that of his nearest rival and includes the league and cup double in 1960/61, three FA Cups, two League Cups, the Cup Winners’ Cup and the UEFA Cup.

Tottenham fans look back with envy to that era when the likes of Bobby Smith and Jimmy Greaves were scoring for fun and north London rivals Arsenal were often a mid-table side (until they won their own double in the 1970/71 season, that is!). It all seems so long ago now though and they have been firmly in the shade of the Gunners for the majority of the last 60 years.

In total, Nicholson won 11 major honours, though perhaps surprisingly, he only ranks as the 10th-best Tottenham manager when looking at win percentages. Nicholson won just over 49% of his games as boss, which is less than many more recent (but far less successful) managers including Andre Villas-Boas, Mauricio Pochettino and Antonio Conte (none of whom won any silverware). Of course, silverware and glory are the only stats that really matter, although Tottenham’s biggest-ever win came in Nicholson’s reign too, a 13-2 drubbing of Crewe Alexander in the FA Cup in 1960.

Keith Burkinshaw, 1976 to 1984

If we focus purely on the number of major trophies won (we won’t count things like the International League Board Cup), Keith Burkinshaw is second only to Nicholson. During his tenure, the Barnsley-born boss won the FA Cup twice (1980/81, 1981/2), the Charity Shield, and the UEFA Cup (in 1983/84, which remains the last time Tottenham won a proper European competition).

Arthur Rowe, 1949 to 1955

Arthur Rowe played for Tottenham almost 200 times but started his managerial career at Chelmsford City. It wasn’t long before he took the manager’s job at his former club though when they were playing in the second tier. He led them to the Second Division title in his first season and then, remarkably, the following term he masterminded what would become Tottenham’s first top-flight title.

Rowe was something of an innovator and Tottenham’s success was largely down to Rowe’s invention of “push and run” football, also known as give-and-go. Essentially, he is credited by many with having invented the one-two in the sport, which is mighty impressive. He also won the Charity Shield with the club in 1951.

Peter McWilliam, 1912 to 1927

We have to go way back into history to find the only other Spurs boss to have won more than one major trophy. Scotsman Peter McWilliam spent most of his playing career at Newcastle United, with whom he won three league championships and the FA Cup. Then when he was manager at Spurs he led them to their second FA Cup and thus became the first player to win the competition as both a player and a manager. He also won the Second Division title and the Charity Shield with Spurs.

Mauricio Pochettino, 2014 to 2019

Although Pochettino didn’t win anything with Tottenham, his tenure was certainly the closest the club have come in recent times. He led the team to two third-place finishes in the Premier League and one second-place finish (in the 2016/17 season, when they finished seven points behind champions Chelsea).

His side also made the semi-finals of the FA Cup twice and lost in the final of the League Cup. The most notable almost-success, however, was that Pochettino led Spurs to their first-ever Champions League final. Agonisingly for Spurs fans, they lost 2-0 to Liverpool in the final… and Pochettino was shown the door just a few months later, since when Spurs haven’t finished above fourth place in the Premier League table and – of course – haven’t won anything!

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