After making it through a group containing Besiktas, Asteras Tripolis and Partizan Belgrade, Tottenham are into the last 32 of the Europa League.
Now, they are faced with a tough test in the knockout rounds, as they take on Serie A side Fiorentina in a two-legged affair this month.
The first game is at White Hart Lane tomorrow, with Fiorentina on a high after beating Sassuolo 3-1 in Serie A last weekend.
It will be no easy task for Mauricio Pochettino's side, with Vincenzo Montella's men having a number of quality players at their disposal - even with the recent sale of winger Juan Cuadrado to Chelsea.
Montella can call upon the likes of Mohamed Salah, Alessandro Diamanti and Khouma Babacar - and Spurs defender Jan Vertonghen told the London Evening Standard that the Florence side have world class players that can harm Tottenham.
"Fiorentina have world-class players, it will be a tight tie and quality-wise we are close to each other," he said. "I've played against them before and they haven't changed - of course, the players have but they are always competing to be in the Champions League."
Tottenham come into the game having won seven of their last ten Premier League games, and with a Capital One Cup final against Chelsea on the horizon, Belgian international Vertonghen is happy with the club's progress as we enter the final few months of the season.
"For us, we’re still where we want to be. It’s a shame we’re out of the FA Cup but we have a final to come in the Capital One Cup, we’re still competing in the Premier League and we’ve got two good games to come against Fiorentina, so we’re in a good way," added Vertonghen.