After Saturday's 0-0 draw at home to Crystal Palace, Manchester United now face the near-impossible task to break into the top four.
Jose Mourinho has remained confident in recent interviews but in order to reach the Champions League spots, the Red Devils must come back from a seven-point deficit- something that has not been achieved before.
Arsenal currently holds the record for the highest point deficit clawed back with five.
The Gunners were sitting in sixth position after 13 games, but an impressive run of results saw Wenger's men pip Tottenham to fourth place by a solitary point.
Mourinho's men would have been put in the same predicament if they had picked up a victory against the Eagles at Old Trafford, but a draw now has the club in uncharted waters.
Can United be record breakers this season?
Only in five other instances have deficits been turned over allowing a team to sneak into the top four as the campaign comes to a close.
Most recently it was Tottenham, who in the 2016/17 season returned the favour on their North London counterparts.
Spurs managed to overtake Arsenal and eventually finish runners-up to Chelsea despite being four points off the top four after 13 games.
Anthony Martial, David De Gea, Antonio Valencia, Chris Smalling, Phil Jones and Andreas Pereira are all approaching the final months of their contracts - in what only adds to the Portuguese's problems.
There are ways in which United can qualify for the Champions League without reaching the top four, however, it does not make for a comfortable read - that is if you are a United fan of course.
The unlikely option is if United can string together a succession of results and win the Champions League trophy, or Jose Mourinho will have to succumb to an early exit from this year's competition and settle for triumph in the Europa League.
Either way, the hostility is most certainly in the air amongst the United faithful.
Do you think United will break into the top four? Have your say in the comments section below.