Since taking over Tottenham Hotspur this summer, Thomas Frank has turned heads with a strong and much-needed turnaround. After last season’s oscillating form — domestic struggles contrasted with Europa League glory — the Danish coach has set about instilling structure, resilience, and consistency in a side that badly needed all three.

Despite their early-season success, they have only faced one ‘Big Six’ side to date, which came in the second week of their campaign. The north London club ultimately went on to win that fixture, with goals to Brennan Johnson and Joao Palhinha helping their side claim a 2-0 victory over Manchester City at the Etihad.

Frank’s side have largely continued that success through the first seven weeks of the season, with them sitting third in the table with four wins, two draws and just one loss to date.

However, they have a tricky start to November ahead, with fixtures against fellow ‘Big Six’ sides Manchester United, Chelsea and Arsenal – all of which come in consecutive gameweeks.

With that in mind, for those who enjoy wagering on big matches with online football betting markets, let’s take a look at each of the above-mentioned match-ups and how they could give us a sense of whether Tottenham are pretenders or contenders in 2025-26.

Tottenham vs Chelsea

Tottenham Hotspur and Chelsea face off at Tottenham Hotspur Stadium on November 1 in what is shaping up to be one of the most closely watched fixtures of the early season. More than just local bragging rights are on the line, as both clubs seek momentum, squad stability, and a chance to make a statement.

While Tottenham currently sit above the Blues in the table (at the time of writing), Chelsea are coming off the back of a last-gasp victory against defending champions Liverpool last time out. Couple that with a 3-0 thumping of Paris Saint-Germain in the Club World Cup final in July, and will Chelsea’s recent success in big games prove too much? Or, will Tottenham show they are the London club to challenge Arsenal’s tilt at the title? We will find out in November.

Tottenham vs Manchester United

Just months after clashing in the Europa League Final, Tottenham Hotspur and Manchester United are set to renew hostilities in a high-stakes Premier League showdown at Tottenham Hotspur Stadium.

The match, scheduled for November 8, carries added significance this season as both sides chase consistency, form, and a position in the competitive top half of the table. While the rivalry has always been fierce, the recent history between the clubs, along with their current trajectories, makes this one of the most anticipated fixtures on the autumn calendar.

Tottenham famously edged Manchester United 1-0 in the aforementioned 2025 Europa League Final in May, ending their 17-year trophy drought and claiming a landmark European title under manager Ange Postecoglou. That result still lingers in the minds of both fan bases and players, and November’s clash offers United a chance at redemption — and Spurs an opportunity to assert dominance once again.

Their last Premier League meeting at Old Trafford ended in a 2-2 draw, but with the fixture returning to North London, Tottenham will look to make home advantage count.

Tottenham vs Arsenal

As the leaves turn and winter edges in, North London braces for one of its biggest showdowns as Arsenal host Spurs on November 23, in a clash steeped in history, rivalry and heavy stakes. This isn’t just another ticket on the calendar. The fixture has narrative, tension, and implications that extend far beyond three points.

For Spurs, they will be looking to claim their first win against their rivals in seven matches, which dates back to May 2022.

Meanwhile, for Arsenal, this is a crucial contest, as they can’t afford to give up too many points in the lead-up to Christmas. Will Tottenham finally get a win over a Gunners outfit that has had the wood over them in recent years? Or, can Arsenal claim their fourth straight victory against their north London foes? Whatever the result, it has all the hallmarks of yet another classic.