The draw for the Europa League playoffs threw up an all-UK clash as Scottish club Hearts were paired with English Premier League giants Tottenham Hotspur.
Hearts sealed their place in this stage of the competition after beating Hungarian club Paksi in new coach Paulo Sergio's first match in charge.
However, the upcoming meeting with last season's Champions League quarter-finalists represents a huge test for the Edinburgh club, in what will be the first-ever competitive meeting of the sides.
Elsewhere, 2010 Europa League finalists Fulham were handed a tricky-looking draw against Ukrainian club Dnipro Dnipropetrovsk, who are coached by former Sevilla, Spurs and Real Madrid boss Juande Ramos.
Birmingham City will meet Nacional of Portugal, while Stoke City's reward for beating Hajduk Split in their first European tie for 37 years is a meeting with Swiss club FC Thun.
Scottish champions Rangers, who were eliminated from the Champions League third qualifying round by Malmo, will meet another Champions League dropout in Maribor of Slovenia.
Celtic will meet FC Sion of Switzerland, and the surviving Irish representative Shamrock Rovers take on Partizan Belgrade.
Other standout ties include last season's Turkish league runners-up Trabzonspor against Athletic Bilbao of Spain, and Hannover, fourth in last season's Bundesliga, against two-time UEFA Cup winners Sevilla.