Levy will celebrate 20 years in the chair on Thursday as Spurs take on Dinamo Zagreb in the first leg of a Europa League last-16 tie at White Hart Lane.
In that time, the chairman has overseen the building of an acclaimed stadium and training complex, enjoyed five Champions League campaigns and yet has won only one trophy, the League Cup in 2008.
Jose Mourinho (left) vows to mark Daniel Levy’s (right) 20 years as Tottenham chairman with a trophy this season
‘I would love to help,’ said Mourinho, the 10th manager or head coach since Levy arrived and fired George Graham. ‘I would love to be part of a work that can deliver a trophy.
‘The work done in this club – independent of the trophies the club didn’t get – is undeniable. The club is a big, big club in many aspects, very well organised, and that’s incredible work from him as the big boss and the whole structure that works for him.
‘I don’t think it’s fair to judge just on the trophies but the trophies are the salt and pepper or football and I would love – not just for him but for the players and the fans and for every one – to help that to happen.
Tottenham’s last piece of silverware came in 2008 when they beat Chelsea for the Carling Cup
JOSE’S COUNTDOWN TO 1000 GAMES
989: Thursday, March 11 – Dinamo (h)
990: Sunday, March 14 – Arsenal (a)
991: Thursday, March 18 – Dinamo (a)
992: Sunday, March 21 – Aston Villa (a)
993: Saturday, April 3 – Newcastle (a)
994: Thursday, April 8 – Europa League QF1
995: Sunday, April 10 – Man Utd (h)
996: Thursday, April 14 – Europa League QF2
997: Sunday, April 17 – Everton (a)
998: Wednesday/Thursday, April 20/21 – First available slot for Southampton (a)
999: Sunday, April 25 – Carabao Cup final vs Man City
1000: Thursday, April 29 – Europa League SF1
1001: Sunday, May 1 – Sheffield Utd (h)
‘I’m not a big guy on stats but my 1,000th official match is going to arrive this season too for a career where I’ve been lucky enough to win so many things, and it would be also nice for him to celebrate my 1,000 official matches by winning a trophy for Tottenham. We are going to try. Let’s see if it’s possible.’
Dinamo Zagreb is match 989 for Mourinho and, if they can progress in Europe and the Premier League fixture against Southampton can be rescheduled in time, the Carabao Cup final against Manchester City will be 999.
A thousand games is a remarkable achievement for any manager, particularly those who survive in elite echelons, although it did feel as if he might be ambushing Levy’s anniversary.
Mauricio Pochettino would tell warm tales about white-water rafting expeditions with Levy – and the pair remain in contact despite his sacking.
Pochettino’s assistant Jesus Perez told the London Evening Standard: ‘Mauricio and Daniel still text each other and they have a very good relationship. At some point, we had to split but we will be back at Spurs for sure.’
Mourinho, however, appears to be in a more formal working relationship between chairman and head coach.
‘I always look to my bosses with utmost respect,’ said the Spurs boss. ‘For one year and a few months our professional relationship is good and he tries to give the best conditions for us.
‘I try to give the best myself and demand the best from everyone who works around me to make the club more successful and better.’
Mauricio Pochettino (left) and Levy (right) still text each other and have a ‘good relationship’