Antonio Conte knew the Tottenham Hotspur job was going to be hard work. Of course he did. After all, there’s a reason he turned down Daniel Levy’s initial offer back in the summer when he first left Inter Milan.

However, when he decided to actually take the job second time round, with Nuno Espírito Santo sacked after just a few months, we don’t think he could have anticipated that it would actually be this difficult.

There was a glimmer of hope, perhaps even what some would call a ‘honeymoon period’ when he first arrived back in London — swapping the blue of west London for the Lilywhite of Spurs — as he guided the side to a nine-game unbeaten streak in the Premier League.

Yes, there have still been some poor results in that time, like the 2-1 defeat away to minnows Mura in the Europa Conference League and the 3-0 loss on aggregate to Chelsea in the semi-finals of the League Cup. But, arguably most importantly, their stock was rising in the league and sites like skybet.com were starting to favour them landing a Champions League spot come the end of the season.

In typical Tottenham fashion though, they’ve managed to capitulate. That lengthy run without defeat in the Premier League culminated with a 2-0 loss at Stamford Bridge, Conte’s old stomping ground, and Spurs went on to lose three of their next four games — suffering embarrassing defeats at home to Southampton and Wolves, as well as a 1-0 loss away to relegation-threatened Burnley.

The defeat to Sean Dyche’s Clarets left Conte sounding like a broken man in his post-match interview, doubting his very own managerial abilities despite having so much success with the likes of Inter and Chelsea — winning a Premier League title and lifting the FA Cup trophy last time he managed in the capital.

“No one deserves this type of situation – the club, me, the players and fans,” the Italian said. “But this is the reality. I came in to try to improve the situation in Tottenham but maybe in this moment, I don’t know, I’m not so good to improve the situation. It’s very frustrating because I know we’re working hard, working a lot and trying to get the best out of every single player.”

To make matters worse, just three days after that defeat to Burnley, Spurs were knocked out of the FA Cup in the fifth round by Middlesbrough — ending any hope of Conte being able to win a trophy with the club this season.

There were no excuses at the Riverside either. Chris Wilder’s Championship outfit were the deserving winners and Tottenham were perhaps lucky to survive for 90 minutes, being dominated in the North East, but somehow holding on to force extra-time — where Boro eventually broke the deadlock through 19-year-old Joshua Coburn.

Another bitter pill to swallow for Conte. Another dent in his immense pride. Another year without a trophy for Spurs — extending their silverware drought to some 14 years since that League Cup win 2008. It’s certainly worrying times for Tottenham, even with Harry Kane, one of the best strikers in the world, and Conte, a top manager, they still can’t seem to hit the right notes and the ‘banter years’ continue.

It’s not something that will be at the front of their minds right now, with still a fair few league games left to salvage some kind of pride. But if Conte and Kane are both to depart the Tottenham Hotspur Stadium this summer, who knows what could happen to the north London club?