Given the rivalry between the two teams the number of managers to have taken charge of both teams is something of a surprise. Plenty of players have done so over the years – that’s an article for another day – and, as we’ve discovered, a fair few have switched from the blue of Chelsea to sit in the Spurs dugout.

Jose Mourinho

The self-appointed Special One enjoyed two spells as Chelsea boss, the first of which began in 2004 and the second nine years later. During a combined five full seasons in charge, Mourinho won three Premier League titles as part of a haul of seven major honours, plus the Community Shield, to establish himself as our most successful manager of all time.

Less than a year after his second departure from the Bridge, he rocked up at Old Trafford to become Manchester United manager, but then in the autumn of 2019 he did the unthinkable – he joined Spurs as Mauricio Pochettino’s replacement. Eighteen trophyless months later, a few days before he was set to lead them out in the Carabao Cup final against Manchester City, Mourinho was relieved of his duties.

George Graham

During his time at Chelsea in the mid-Sixties as part of Tommy Docherty’s collection of ‘Diamonds’, Graham had two cracking nicknames: Gorgeous George, for his dashing good looks, and Stroller, for his languid, easy-on-the-eye style. He scored 46 times in 102 appearances for the club, winning the League Cup in 1965, before joining Arsenal.

Of course, Graham famously managed the Gunners too, and when he was linked with the Chelsea job in 1996, the fans politely told Blues chairman Ken Bates to stick the Scot where the sun doesn’t shine. Two years later, he ended up taking over at Tottenham, whom he led to League Cup glory a few months into his tenure.

Glenn Hoddle

When Graham was unceremoniously dismissed by Spurs in 2001, the club turned to one of its greatest-ever players – and a man whose best days in management had come with Chelsea, during a three-year spell at the Bridge in which he brought the club kicking and screaming into the modern era, as well as reaching a first FA Cup final for 24 years.

Hoddle had needed to win over the Chelsea faithful when he was appointed player-manager in 1993, but he had no such problems when he went back to Tottenham to manage his boyhood club. Alas, after a couple of mid-table finishes he left Spurs and has since gone on to become a prominent pundit.

Terry Venables

Everyone thinks of El Tel as a Spurs man through and through, as he both played for and managed the club. In reality, Venables played more league games for Chelsea than any other team during his playing career, having come up through the ranks and become the on-field leader of the aforementioned Doc’s Diamonds in the Sixties. Had he not fallen out with his manager, who knows how long his association with Chelsea would have gone for.

Instead, he left to join Spurs and he won the FA Cup with the club as a player, before repeating the feat as a manager in 1991. Incidentally, that is one of three major honours Tottenham have won over the past three decades and, with Graham delivering another of those, that just leaves Juande Ramos as the odd one out.

Andre Villas-Boas

Ten years have passed since AVB took charge of the Blues, having previously worked for the club as part of Mourinho’s backroom team. He’d just completed a dream season as Porto boss and, inevitably, the comparisons with his old boss were never far away. Unfortunately, the results on the field could not stand up to what Mourinho had achieved, and he left Chelsea midway through his maiden campaign at the Bridge.

In the months that followed, his replacement, Roberto Di Matteo, took us to FA Cup and Champions League glory. A few months later, Spurs took a punt on Villas-Boas and he led them to a fifth-place finish, before being sacked in December 2013, to the surprise of many – at the time, he had the highest win percentage of any Spurs manager in the Premier League era.