Tottenham are one game away from reaching the Europa League group stage after beating a stubborn Shkendija side 3-1 in North Macedonia.
Erik Lamela hit the opener after just five minutes when Son Heung-min found the Argentinean unmarked inside the box.
But Jose Mourinho's men failed to build on their early lead as Shkendija put bodies behind the ball. Toby Alderweireld and Serge Aurier both went close with headers, but the Macedonian side kept the deficit to just one until the half-time whistle.
Valmir Nafiu then shell-shocked Spurs after blasting past Joe Hart on his Spurs debut.
Agim Ibraimi almost gave the hosts the lead eight minutes later after heading just wide, but Mourinho's blushes were spared when Son converted the rebound after Lucas Moura's shot was saved.
Jose Mourinho: 'The goals were too small'
Substitute Harry Kane then made sure of victory after heading home Son's cross.
Spurs will face Maccabi Haifa at home in the Europa League play-off round.