ACF Fiorentina held Tottenham Hotspur to a round of 32 first-leg 1-1 draw in the Europa League at the White Hart Lane and the Premier League side now faces a battle to remain in the European league.
Roberto Soldado volleyed in a sixth-minute opener from Paulinho's corner to give Tottenham the lead and help them dominate the opening half-hour.
However, Argentine centre-back Jose Maria Basanta scrambled in an away goal to give Vincenzo Montella's side the edge ahead of next week's second leg, the BBC reported.
Nacer Chadli hit the bar for Tottenham, who faded after half time, as both the sides failed to score another goal.
Soldado started instead of 23-goal top scorer Harry Kane as head coach Mauricio Pochettino, facing the first of six matches in 17 days, made six changes in an attempt to keep his squad fresh.
At first, it looked as though his rotation would pay off, however, the game disappointingly ended in a draw.
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Tottenham head coach Mauricio Pochettino said that he believes they deserved more, adding that his side created more chances in the first half and dominated the opening 45 minutes.
Pochettino added that he is happy with the performance but disappointed with the result, insisting that they need to go to Florence to try to win the game and progress.
