Tottenham, Manchester United, and Everton
The second set of back-to-backs that stand out on the schedule occurs at the end of October and the beginning of November. On Saturday, October 30, Spurs host Manchester United and then travel to Merseyside the following weekend to face Everton on November 6.
In the build-up to the Manchester United match, there is supposed to be a midweek Carabao Cup tie, assuming Tottenham makes it to the 4th round. Then in between the two matches, Matchday 4 of the Conference League is scheduled.
Once again, Tottenham is likely to be playing these teams on limited rest. Fortunately, United will also be playing in Europe and should have a match as well. Everton on the other hand is not going to be in Europe and, like Arsenal before them in September, will be the fresher team against Spurs in the second of a big set of matches.
The second pair may be crowded or it may not be for Tottenham
Spurs again play Everton and United back-to-back in March. First Tottenham hosts Everton on Saturday, March 5 before trekking north to Manchester to face United at Old Trafford on Saturday, March 12.
Again, fixture congestion may be an issue or it might not be depending on how things go. In the week prior to the Everton match, the FA Cup 5th round is scheduled to be played. As it were this past season, Everton and Tottenham faced off in a 5th round classic that the Toffees pulled out.
In between the two league matches is supposed to be the first leg of the Europa Conference League Round of 16. Of course, to get there, Tottenham needs to qualify for the Group Stage from the Playoff and then qualify for the Round of 16 from the Group. Likely a very big possibility but still something that needs to be accomplished.
It is also likely that Everton would still have the extra domestic competition at that point and United would be in some kind of European affair, even if just the Europa League after another 3rd place finish in the group stage.
Regardless of the congestion, those matches in early March are going to be huge, just like they are in late fall.
The last pair of matches should be familiar for Tottenham and hopefully create some motivation.