Manchester City have to overturn a 14-point gap at the top of the Premier League table to retain the title - something which has never been done in English top-flight history.
Goals from Anthony Martial and Marcus Rashford gave Ole Gunnar Solkjaer's Manchester United the bragging rights against rivals City on Saturday, keeping Liverpool well clear after their 3-0 win over Bournemouth.
However, even with 22 games still to play in the Premier League season, Manchester City will need to become the first team in top-flight history to overturn a 14-point gap at the top of the table if they want to retain the title.
While Manchester City will have to enter the history books to win the Premier League title, Saturday's defeat saw manager Pep Guardiola set a new record low points tally in his career.
The Citizens are on 32 points from their opening 16 games - the worst total that Guardiola has picked up in the same amount of games during his 11-year career as a manager.
Things could get worse before they get better for Manchester City too as they face Arsenal, Leicester City and Wolves in their next three games in the Premier League.
If Guardiola's side continue to struggle over the next few weeks then they could be outside of the top four at the turn of the year.
In between their games in the Premier League, City also face a trip to Dynamo Zagreb to round off their