Gareth Bale spent seven years at Real Madrid but departed at a low point in his LaLiga career, hoping a loan to Tottenham proves a success.
Spurs laboured to a 3-1 win in North Macedonia, though they may have been thwarted by smaller goalposts if not for Jose Mourinho.
Manchester United are reportedly still eyeing Jadon Sancho before the transfer window closes.
Real Madrid allowed Gareth Bale to rejoin Tottenham last week and Juande Ramos has defended the Wales forward's time at the club.
Son Heung-min was again Tottenham's attacking hero as a goal and two assists carried Jose Mourinho's side past Shkendija.
Sergino Dest reportedly has his heart set on LaLiga champions Barcelona, despite interest from Bayern Munich.
Tottenham boss Jose Mourinho will look to move into international management one day, though is unsure over coaching his native Portugal.
Last week's narrow win over Lokomotiv Plovdiv showed why Tottenham "cannot take risks" at Shkendija, according to Jose Mourinho.
Tottenham coach Jose Mourinho says Dele Alli - linked with Real Madrid and Paris Saint-Germain - must take responsibility for his form.
Barcelona veteran Luis Suarez is reportedly poised to move to Atletico Madrid.