Tottenham Hotspur have been drawn against Manchester City in the quarter-finals of the Champions League, meaning Mauricio Pochettino's side face the daunting prospect of playing the Citizens three times in just 11 days.
Tottenham are looking to secure a vital top four finish in the Premier League, whilst the Champions League is now their most viable source of a trophy this season following their elimination from both the Carabao Cup and the FA Cup.
The first match against City comes on April 9 in the home leg of their European tie, before the return leg at the Etihad Stadium on April 17, in what will undoubtedly be a challenging period for Pochettino's men.
Just three days later on April 20, they will return to Manchester to face Pep Guardiola's reigning champions in the league, with City looking to retain their lead over Liverpool in the Premier League table.
However, before the meetings with City, Tottenham will also travel to Anfield on March 31 to face Jurgen Klopp's side, who will be desperate to earn a positive result as they await a potential slip up from the league leaders.
A clash with Huddersfield Town also features during this three-week spell, whilst Tottenham are also scheduled to face Brighton and Hove Albion on April 6, although this could be postponed if the Seagulls advance in their FA Cup tie with Millwall on Sunday.
Pochettino's men currently sit third in the Premier League standings, just one point ahead of fourth-placed Arsenal. Both Chelsea and Manchester United are also incredibly close behind, meaning just one poor result could ultimately prove catastrophic to Tottenham's top-four dreams.
League defeats against both Liverpool and City, coupled with positive results for their rivals, could leave Tottenham sixth in the table, but Pochettino cannot afford to rest his stars as they face four incredibly important matches.