The Lilywhites do have a decent start to the campaign when looking at their opening eight fixtures but they face a tricky start with Everton the visitors to N17 on Sunday.
While it was perhaps a bit too easy for the team last time out against the Toffees in July, Carlo Ancelotti’s team should be a different prospect altogether following the summer additions of Allan, James Rodriguez and Abdoulaye Doucoure.
Spurs themselves have been busy in the transfer market with three players coming in through the door and Mourinho has to decide whether or not they start on Sunday.
But what other decisions does the head coach need to make between now and then? football.london takes a look.
The formation of choice under both Mourinho and Mauricio Pochettino at Tottenham has tended to be 4-2-3-1.
Spurs have lined up this way throughout pre-season but they do have the players to be able to switch to 4-3-3 if the boss elects to shake things up.
Many fans want a midfield three of Pierre-Emile Hojbjerg, Giovani Lo Celso and Tanguy Ndombele as the summer signing can play the holding role to let his two teammates push on and really have a big impact in the final third.
It definitely does remain an option for Mourinho going forward but Dele Alli’s form in pre-season may give him no choice but to stick with the usual 4-2-3-1.
The 24-year-old has looked very sharp and he could well cause the visitors a number of problems if he plays behind Harry Kane.
Mourinho does have a big decision to make in the middle of the park for the game against Ancelotti’s side.
As Lo Celso is 50/50 for the game because of a hamstring issue, it’s a question of who he starts in midfield with Hojbjerg now an option following his move from Southampton.
The Dane is expected to start and it looks like it will be one of Harry Winks or Moussa Sissoko who partners him if the Argentine isn’t declared fit enough to play from the off.
Well, it may be the latter who gets the nod as the former has only featured once in pre-season for Spurs and was then forced to withdraw from the England squad for their UEFA Nations League games.
Spurs haven’t confirmed as to why Winks was absent but he has trained with the squad this week in preparation for the match.
It’s a tough choice for Mourinho to have.
Bergwijn or Lucas?
The Brazilian has been a regular since Mourinho’s arrival last November but he really is going to have to start chalking up goals and assists on a regular basis as the Dutchman will be breathing down his neck for a starting spot.
Lucas didn’t manage to find the net in pre-season and he needs to hit the ground running if he is to keep his place in the side.
It may be an easy decision for the boss at present but it could become a whole lot harder as the weeks go on.
Stopping Rodriguez and Co
Everton will be looking to start the season off in style following their business in the transfer market.
Midfield was a major issue for the Blues in their last game at Tottenham Hotspur Stadium and it was rather all too easy for the hosts.
Ancelotti has certainly upgraded his choices in the middle with Allan, Doucoure and Rodriguez all outstanding options following their moves to the club.
Mourinho has to find a way to keep them all quiet if they go straight into the starting XI as the likes of Richarlison and Dominic Calvert-Lewin could flourish playing off them as the team’s creativity will increase dramatically as a result of their transfer business.
Nullifying Rodriguez is a must and Hojbjerg could have an important role in midfield given the amount of ground he covers.
Mourinho’s bench dilemma
The new season has seen a slight change to the rules we had a few months ago following the restart.
Due to the amount of games in such a short amount of time in order to finish the season, teams were allowed to name nine substitutes on the bench and make a total of five changes.
While that was good for those who have large squads, some struggled to name substitutes and a few even had to name two goalkeepers just to make the numbers up.
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Well, it’s back to the usual seven substitutes and three changes for the new campaign.
That in turns makes things rather difficult for Mourinho as he will have to give a few players the bad news that they haven’t made the squad against Everton.
The likes of Ryan Sessegnon, Serge Aurier and Gedson Fernandes could be at risk due to the large numbers.