Dominating the game in Bulgaria but failing to find the crucial breakthrough, it was the hosts who opened the scoring with 20 minutes left to put the Lilywhites on the brink of an embarrassing early exit.
However, goals from Harry Kane and Tanguy Ndombele ensured that didn’t happen as they sealed their passage into the next round to set up a tie against Shkendija.
Well, Spurs will discover very soon who they will face in the crucial play-off round providing that they advance beyond their Macedonian opponents next Thursday.
The draw is taking place at 1pm at the House of European Football in Nyon, Switzerland and there is the possibility of coming up against Steven Gerrard’s Rangers side.
Tottenham and Shkendija are ball number two in the seeded part of group four in the main path, with Galatasaray and Hadjuk Split ball one, Standard Liege and Vojvodina ball three and APOEL and Zrinjski ball four.
Rostov and Maccabi Haifa are ball five in the unseeded draw, with Willem II and Rangers ball six, Fehervar and Reims ball seven and FCSB and Slovan Liberec ball eight.
During the draw the balls containing the names of the seeded teams will be placed in one bowl and the balls containing the names of the unseeded will be put into another bowl.
One ball will be taken from each bowl and placed in a large empty bowl in the middle, where they will be shuffled. The first team drawn will play the tie at home.
The match will take place on October 1, with extra time and a penalty shoot-out if required.
All qualifying ties will be single-leg matches once again and the winners advance to the UEFA Europa League group stage.
To find out who Tottenham will face next month, check back on football.london later for our live draw blog.
Could it really happen? Could Gareth Bale return to Tottenham?
It could happen Tottenham fans, football.london sources say the club are exploring a loan deal with Real Madrid.
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Details of all the teams in Tottenham’s group can be seen below.
1 Galatasaray (TUR) / Hajduk Split (CRO)
2 Shkëndija (MKD) / Tottenham (ENG)
3 Standard Liège (BEL) / Vojvodina (SRB)
4 APOEL (CYP) / Zrinjski (BIH)
5 Rostov (RUS) / Maccabi Haifa (ISR)
6 Willem II (NED) / Rangers (SCO)
7 Fehérvár (HUN) / Reims (FRA)
8 FCSB (ROU) / Slovan Liberec (CZE)