Predicting Tottenham's next five Premier League results as first win approaches

Tottenham are still searching for their first Premier League win of the season under Roberto De Zerbi, and we have predicted the results of their next five fixtures based on form, head-to-head records and home and away performances, starting with Coventry City on Monday. Monday 19th October Premier League Saturday 24th October Premier League Saturday 31st October Premier League Saturday 7th November Premier League Saturday 21st November Premier League 1.
Tottenham Hotspur vs Coventry City, 19 October Tottenham Hotspur were widely tipped to finally secure their first Premier League win when they welcomed newly promoted Coventry City, who had been struggling for form this season. However, Coventry took little kindly to being viewed as an opportunity for Spurs to get back on track, responding by thrashing Newcastle United 4-1 on Monday.
That result has taken some of the favouritism away from Tottenham ahead of next week's meeting. Even so, Spurs have played some really good football this season, often doing enough to deserve more than they have taken from their matches.
A team sitting 19th in the table should not be creating the opportunities Tottenham have, but their inability to finish those chances has repeatedly let them down. The encouraging part is that finishing is an area De Zerbi can work on, and the nine-day gap since the dramatic draw against Manchester United should give his players valuable time on the training ground.
Coventry will arrive in north London with renewed confidence, but Tottenham should have enough quality to come out on top if they are more clinical in front of goal. The two sides have not met in the Premier League since the 2000/01 season, so there is little to take from their head-to-head record.
Chelsea vs Spurs, 24 October Spurs could change every player in their starting XI, replace the manager and arrive at Stamford Bridge in the form of their lives, but would probably still find a way to lose there. Their last victory there came under Mauricio Pochettino in April 2018, when Dele Alli scored twice and Christian Eriksen added another in a 3-1 win.
The four managers who have taken charge of the fixture since then, including De Zerbi, have all struggled to change that record. More broadly, Tottenham have not won a competitive match against Chelsea since February 2023.
Chelsea, meanwhile, are enjoying a strong start to their first season under Xabi Alonso, most recently putting five goals past Bournemouth. De Zerbi's 10 men did manage to beat Alonso's side in a pre-season friendly during the summer, but replicating that result at Stamford Bridge against an opponent in considerably better form will be a much tougher proposition.
Tottenham Hotspur vs Crystal Palace, 31 October Following the difficult trip to Chelsea, Tottenham will have a more favourable opportunity to pick up points when Crystal Palace visit north London. Crystal Palace have made a decent start under new manager Pierre Sage, sitting 12th in the Premier League table with seven points from six games.