Tottenham have been given the unenviable task of facing Manchester City three times in the space of 12 days next month after they were drawn against each other in the Champions League quarter-finals.
The two English sides were pitted against one another in Nyon on Friday morning giving Spurs the headache of playing City at the Etihad twice in the space of three days.
Spurs will play the first leg of their quarter-final tie at home with the match set to be played on April 9 at their brand new 62,000-seater stadium.
The second leg will then be played at the Etihad a week later to determine who will proceed into the semi-finals of Europe's elite club competition.
In between the two-legged encounter, both City and Spurs will also have a Premier League fixture to manage.
Tottenham host Huddersfield at home while City travel to south London to face Crystal Palace at Selhurst Park.
Once the second leg has been played on April 17, Mauricio Pochettino's men will then show their top-four credentials three days later when they travel to the Etihad again for their Premier League encounter with City.
With Pep Guardiola's side currently in a tight battle for the Premier League title, it remains to be seen how the Spaniard will prioritise the run of games against Spurs.
City are only one point ahead of Liverpool in the title race but it is well known that the Champions League is the only bit of silverware missing from the club's trophy cabinet.
Meanwhile, Tottenham are just one point above fierce rivals Arsenal in third and are still yet to play Liverpool at Anfield at the end of March.
Defeat in the Europe for Spurs will see them go yet another season without any silverware while chairman Daniel Levy will be desperate to have Champions League football in their first full season at the new White Hart Lane.
However, the omens are with Spurs as City have lost each of their four games against English opponents in European competition.
City lost twice against Chelsea in 1971 and then famously crumbled again over two legs against last year's finalists Liverpool.