Those with a sense of deja-vu heading into this fixture will not be alone; this is the 11th time these two sides have met on the opening weekend of a top-flight season, which is three more than any other fixture.
The Tottenham curtain-raiser comes as football fans are given the chance to watch behind-the-scenes footage of their 2019-20 campaign play out on their TV screens, and the capital outfit will be hoping for a smoother journey on and off the pitch this time around.
A return to the top four must be their main goal for the season, but there is plenty of work to do if they are to bridge the seven-point gap which ultimately separated them from Chelsea last season - particularly given the improvement of some of the teams above them.
Mourinho will be the first to tell people that his squad was beset by injuries last season and he will be confident that lightning can't strike twice - at least not to such devastating effect - while he will also take encouragement from his side's progress after he took over.
A sixth-placed finish was not terrible considering they were 14th when Mourinho arrived, and a six-game unbeaten streak to end last season provides more cause for optimism.
That run began with victory over Everton at home to stretch their unbeaten streak against the Toffees to 15 games, going back to December 2012.
Everton's record away to Spurs is even worse; they have won just three of their 28 such games in the Premier League era - losing 17 - and the last of those wins came in November 2008, 11 visits ago.
Like Spurs, the Merseysiders have cause for optimism heading into the new campaign, though, having shown improvement under their own world-class manager and also done some eye-catching business during the summer.
James Rodriguez is the most high-profile signing as the former Real Madrid and Bayern Munich playmaker attempts to revive his career in the Premier League, adding a sprinkle of stardust to a team Ancelotti is slowly moulding into his own image.
A significant improvement on last season's 12th-placed finish is expected, and Ancelotti is confident enough to have publicly declared that he is targeting a top-six finish - something Everton have not achieved since 2013-14.
Victory in North London over one of their top-six rivals would certainly be a good start towards that goal, particularly as Everton's away record last season left a lot to be desired - only the bottom five picked up fewer points on the road.
By contrast, Tottenham's home record was bettered only by Liverpool and Manchester City, including wins in their last four league games on their own turf.
Spurs have also been in encouraging form in pre-season with victories over Ipswich Town, Reading and Birmingham City, although defeat to Watford in their last warm-up game ruined their perfect record.
Everton, meanwhile, fell 3-0 down to Blackpool within 12 minutes of their opening pre-season game, but recovered to draw 3-3 and then beat Preston North End in their most recent friendly.
Tottenham Hotspur pre-season form: WWWL
Everton pre-season form: DW
Harry Kane - scorer of eight goals in his last five games against Everton - is fit to lead the line and Dele Alli is expected to support him in the number 10 role, while Steven Bergwijn will be pushing for a start ahead of Lucas Moura.
Tottenham Hotspur possible starting lineup:
Lloris; Doherty, Alderweireld, Dier, Davies; Hojbjerg, Sissoko; Bergwijn, Alli, Son; Kane
Everton possible starting lineup:
Pickford; Coleman, Keane, Mina, Digne; Gomes, Allan, Doucoure; Rodriguez; Calvert-Lewin, Richarlison
We say: Tottenham Hotspur 2-1 Everton
Everton have plenty of quality in their team now and look like a side capable of getting points from these type of matches as the season goes on.
However, at this stage it is difficult to look past the respective home and away records from last season, which both firmly point to a Tottenham win in this match.
Top betting tipOur expert tipster partners at Sporita.com are predicting over 1.5 goals in this match. Click here to find out what else they are predicting for this game and for more of their tried-and-tested football tips.Over 1.5:data
Watch the Sports Mole Football Shorts prediction for this game below: