|Van der Vaart has scored 10 Premier League goals and two in the Champions League for Spurs [EPA]
Tottenham Hotspur travelled to Italy with big concerns in midfield and the added worry that Rafael van der Vaart would not be fit for their European Champions League last-16 game with Serie A leaders AC Milan.
Gareth Bale, who lit up the San Siro with a hat-trick last time Spurs were in the city, when they lost 4-3 to Inter in the group phase, misses Tuesday's first leg with a back injury, while Jermaine Jenas is suspended.
Meanwhile Spanish legend Raul Gonzalez has an emotional return to his homeland as his Schalke 04 side travel to two-time runners-up Valencia.
For Spurs, Luka Modric is struggling to make the starting side as he recovers from an operation to remove his appendix less than two weeks ago.
The Croat's injury piles the pressure on Van der Vaart to overcome a calf strain that kept him out of Saturday's 2-1 English Premier League win at Sunderland.
"I have got to see how Rafa is," manager Harry Redknapp said of the Dutchman, who has been in superb form since signing from Real Madrid last summer, scoring 10 league goals.
The return to the first team of Niko Kranjcar, who has scored the winning goals in Spurs' last two games, also gives Redknapp an attacking midfield option.
"Niko deserves his place in the team," Redknapp said after the Croat's second successive sweetly-struck winner.
"He's a top player. He practises, he spends time after training every day. Every day, he is on the training ground after he finishes doing a half-hour's practice."
If things don't go as planned for Milan, coach Massimiliano Allegri may look to the players in the stands and think what might have been.
Two league draws in a row for the Italian pacemakers were followed by Saturday's 4-0 romp against Parma, with cut-price January recruits Antonio Cassano and Mark van Bommel playing a part in the victory.
The pair, along with former Ajax player Urby Emanuelson, are ineligible to play for the seven-times winners in the Champions League having featured in earlier rounds with Sampdoria and Bayern Munich.
Milan knew this when they signed them but the pursuit of their first scudetto since 2004 takes precedence over European competition this season.
"We're first in the championship for the first time in years so it's logical to think Milan's objective is the league title," Allegri said.
Cassano's absence means Allegri is set to play Zlatan Ibrahimovic, Robinho and Alexandre Pato as his front three.
Midfielders Andrea Pirlo and Massimo Ambrosini miss out due to injury and the combative Van Bommel could at least have patrolled the area in front of the back four.
In the night's other tie Raul is hoping for a successful return to Spain as Schalke look to seize the upper hand in a tie between two of the lesser fancied teams left in the competition.
The 33-year-old ended his 16-year love affair with Real Madrid in the summer to join the Germans.
"It certainly won't be easy but, personally, I've got good memories from playing there," said Raul of Valencia’s Mestalla stadium.
"Valencia are a great team but this is going to be a very even tie.
"It's a really great incentive for me especially playing against such a strong rival and in a stadium that generates a great atmosphere.
"It's an extraordinary setting to play a Champions League game."
Valencia are third in the Spanish Primera Division after winning 2-1 at Atletico Madrid on Saturday and have the better pedigree in this competition having reached successive finals in 2000 and 2001.
Coach Unai Emery has managed to keep the team moving forward despite the summer sales of Spanish World Cup stars David Silva and David Villa.
Villa's replacement Roberto Soldado has been a major factor behind their progression to the knockout phase.
Soldado is his team's top scorer with five goals in the group stage and the former Real Madrid man gets good service from speedy wingers Juan Mata and Joaquin.