Tottenham face tricky opposition in Italy's most decorated club Juventus, as the Champions League knockout's get underway in Turin.
The Lilywhites cruised to top spot in their 'group of death' beating Real Madrid and Borussia Dortmund along the way.
It has been seven years since Spurs played in the Champions League last 16, and that came against AC Milan in which they won 1-0 over the two fixtures.
The Italian outfit currently sit second in Serie A as they continue to chase the impressive Napoli.
Spurs face an established side in the six consecutive Italian champions who also featured in last seasons Champions League final, where they lost respectively to Real Madrid.
The Italian champions will prove a challenge for the high flying Spurs as they have a very well balanced team.
A strong defence will be sure to provide Harry Kane with one of his biggest challenges to date with the solid Giorgio Chiellini leading the back line.
Spurs have had a mixed bunch of results in their previous trips to Italy, losing against Inter and Fiorentina but enjoying a 1-0 victory at the San Siro over AC Milan.
Group of death success
For many Spurs fans having reached the final 16 may have come as a surprise due to the challenging group in which they were drawn.
However, victories over Real Madrid and Borrusia Dortmund were testament to the superb attitude and performances against some of Europe's elite.
Despite an impressive group stage, Juventus will arguabley provide Spurs with their toughest test to date due to Real Madrid not quite reaching the heights we have all come to expect from them this year.
Juventus' key players
With Paulo Dybala expected to miss the game, Gonzalo Higuaín will provide the hosts' main goal threat.
Having scored 14 league goals this season the Argentine will be looking to add to his tally of two Champions League goals for the season.
Meanwhile, at the other end of the pitch Gianluigi Buffon looks to end his final season in football with a bang with the Champions League trophy the only missing from his list of honours.
The Juventus side holds great strength and balance in all aspects of their game meaning Spurs will have to continue their recetn fine form if they want to give themselevs a chance of progressing.
Having missed three months of football, defender Toby Alderweireld is expected to be left at home despite recently returning to first team football.
It will come as a blow to Spurs fans but his lack of football in recent weeks may have forced Mauricio Pochettino into leving the Belgian behind.
However, some good news for Tottenham is Argentine international Paulo Dybala is expected to miss both fixtures due to a hamstring injury.
Also, Frenchman Blaise Matuidi will miss both fixtures as he too is suffering from a hamstring injury.