Last season, in Ange Postecoglou’s first campaign, Tottenham managed to re-establish their reputation as pioneers of exciting, attacking football after a spell of trophy-hunting campaigns under José Mourinho and Antonio Conte, which did not amount to anything and were punctuated by an even sorrier spell under Nuno Espírito Santo.

Spurs’ exciting football under Postecoglou, however, arrived at the expense of just enough stumbles to deprive them of a Champions League spot, with many making the argument that a bit of pragmatism could have helped Spurs overcome the two-point deficit over fourth-placed Aston Villa, who themselves had a horrid run in the last two months of the season and in any other year could have tumbled out of the top four.

This time, criticism will come their way with more ferocity if the Lilywhites fail to make the top four, which is very much a possibility given the way their starting results have gone. One can make the argument that the Australian coach’s peculiar “my way or no way” approach to football is hardly equipped to help the club achieve long-term success of they manner they desire, and yet Postecoglou’s never-giving-up men are capable of beating anyone of their day.

And so, here we look at their biggest games over the coming months that, should they win them, will leave them in a strong position for Champions League qualification going into the business end of the season.

Beating these sides will only hand Spurs the crucial points and confidence, it will also take away points from their direct competitors, leaving their fate very much in their own hands.

So let’s have a look at these fixtures.

Man City v Tottenham | November 23

Because they have had the league title in the bag for the past four years, many often forget that Man City tend to take their time to get going in the early weeks of the season, and of course once they hit momentum, it’s over.

Man City’s form has not been horrid this season by any means, but they’re not on top. Injuries to key players have further worsened their case, and while this weakened Sky Blues outfit is still capable of pulling any team apart when on song, they are by no means invincible, as demonstrated by their recent defeats to Bournemouth in the league and Sporting in the Champions League.

On the other side of the upcoming international break, Spurs will have a golden opportunity to take City apart while they have the chance. They will want to draw inspiration from their recent victory over the Cityzens in the Carabao Cup to keep them as away from the top as possible while keeping them in their sights as they hunt down that top-four finish.

Tottenham v Chelsea | December 8

Chelsea have been surprisingly stable in the first quarter of the season, and credit for that goes to Enzo Maresca, whose ruthless skimming of the bloated Blues brigade, along with his tactical application that helped him deliver the Championship title to Leicester City last season, has resulted in results consistent enough to land Chelsea back into the Champions League conversations for this term.

And it’s not like Tottenham and Chelsea have needed a Champions League narrative for their meet-ups to become feisty affairs in recent years. Going into the hectic festive period, this game may very well set down the marker for how the two sides will fare over the two most exhausting months of the English football calendar and hand the kind of momentum that could take them to the promised land instead of making them bridesmaids again.

Tottenham v Liverpool | December 22

Liverpool have had very little teething issues while adjusting to life under their new head coach, Arne Slot. The table-topping Reds have set the early-season momentum and have made themselves unavoidable as far as the title conversations are concerned.

Tottenham may not have enough in the tank to challenge Liverpool for the league this time round, but if they can take them apart on this day, they will be doing both themselves and their competitors a favour. On paper, they most certainly have the potential to achieve this, regardless of how ominous the Red march might look right now.

Arsenal v Tottenham | January 16

North London Derby. Need one say more?

The Gunners took the bragging rights when these two sides met almost two months ago, though they haven’t really been able to run away from their fiercest local rivals and currently lie just two points ahead of them.

Tottenham will have revenge and Champions League nights on their mind when they meet Arsenal in January, at which point Mikel Arteta’s men will not only be involved in the Champions League but will also be keen to make sure they don’t get left behind too far from the title-chasing pack—a kind of pressure Tottenham do not have, and so they could hurt Arsenal as they try to secure their standing on multiple fronts, take back the bragging rights, and inch closer to that top-four finish.

Tottenham v Man City | February 26

This is that time of the season when the Man City train start running away with unstoppable momentum. This, incidentally was also the period last season around which time the wheels started coming off Spurs’ pursuit of the Champions League.

This fixture will turn out to be a sliding doors moment. If City win this, they will go on to reassert themselves in the title race, for even at their wounded worst they will not be too far away from the top. If Spurs manage to get the better of them, the victory will reinforce their belief that their destiny is in their hands going into the final months of the season.

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What do you think of our picks? Do you think there are other fixtures in this period that will turn out to be more crucial for Spurs as they hunt down that top-four finish?