Thomas Frank will be hoping that history doesn't repeat itself, given the number of injuries Tottenham suffered last season. A plan needs to be drawn up to find a replacement, either by looking in-house or buying a player from elsewhere.
There isn't anyone at Spurs with Maddison's particular skill set, but it's unclear if Daniel Levy and the board will approve further spending this summer. If not, Frank may look to Pape Sarr to provide something different.
Sarr has been playing a more pivotal forward role in pre-season, scoring an impressive long-range effort against Arsenal. Chris Waddle believes he could be the answer to Tottenham's prayers, citing his energy levels, confidence, and ability to run off the ball.
Another option could be James McAtee, who is close to a deal with Nottingham Forest. He has the natural ability to fill the void left by Maddison's injury, and his passing ability is impressive.
McAtee's asking price is reportedly £40m, which could be a bargain given his peak years are well ahead of him. However, if Tottenham move too late, they may miss out on McAtee and be left with limited options.
Harvey Elliott could be another consideration, but his output has been limited, and his energy can't be questioned. The 50% shooting accuracy and 33.3% conversion rate are stats worth looking at in more detail.
Mikkel Damsgaard is another option, known to Thomas Frank from his time at Brentford. The 25-year-old has been a key factor in the Bees' success, providing 10 assists in 38 top-flight games last season.
However, negotiating with Brentford could be tough, especially after they've already lost several key players.