When Tottenham Hotspur reached the Champions League final in 2019, it seemed as if this achievement could have provided them with the platform to push on as a club in the following seasons.
However, Spurs have unfortunately gone backwards since losing to Liverpool in this competition as they are no longer a shoe-in for a top-four place in the Premier League.
Whilst Tottenham's lack of progress may be blamed by some on the club's lack of consistency on the pitch, their transfer recruitment has been relatively poor in recent years as both Jose Mourinho and Mauricio Pochettino have struggled at times in the market.
Despite spending large amounts of money on the likes of Davinson Sanchez, Steven Bergwijn and Erik Lamela, this particular trio have ultimately failed to set the Premier League alight.
Indeed, some of Tottenham's best imports of the Premier League era, such as Son Heung-min and Luka Modric were plucked from relative obscurity for respectable sums before going on to have a major impact in North London.
Here, in our quiz, we take a look back at 15 of Spurs' signings over the years and ask you to match up the player with the manager who signed him.
Do you reckon you can get every question right?
Have a go below!