Forgotten man Erik Lamela scored twice against Toronto to give Spurs their first pre-season victory under new boss Mauricio Pochettino.
Ben Davies made his first appearance in a Tottenham shirt as Spurs beat Toronto FC 2-3 thanks to a winning goal from substitute Andros Townsend.
Tottenham’s new left-back signing was joined by Cristian Eriksen and Kyle Walker, who made their first pre-season appearances at BMO Field.
Toronto FC, captained by former White Hart Lane hero Jermaine Defoe, had fought back from a two-goal deficit following a brace from Argentine forward Lamela.
In the second game of their US and Canada pre-season tour, Spurs dominated the first half with brilliant possession play from Aaron Lennon and Eriksen.
Lennon and Lamela both squandered chances in the opening stages, but the Argentinian made no mistake finding the net after 16 minutes.
A Lennon pass was cleverly dummied by Roberto Soldado into the path of the club’s record-signing, and he coolly slotted past Chris Konopka.
Solid defending from centre-back pairing Younes Kaboul and Milos Veljkovic helped stifle a lacklustre Toronto side as they struggled to get a hold of the first-half.
Five minutes from the interval, Lamela grabbed his second when his marauding run into the home team’s box was spotted by Soldado, and the winger’s emphatic finish established a comfortable 2-0 lead.
Ten changes from Pochettino at the break saw the sides far more evenly matched, with all but Brad Friedel making way for Spurs.
A superb last-ditch tackle from youngster Zeki Fryers denied Toronto’s Jonathan Osorio a clean sight of goal, but the Canadians grabbed their first on 65 minutes through substitute Wiedeman.
A cunning through-ball from Daniel Lovitt beat the defence and the Toronto attacker finished well past Friedel.
Now with a boost of confidence, Toronto equalised after the 70 minute mark as Wiedeman teed up Bekker’s long ball for Hamilton to slot home.
Spurs replied positively with Kyle Walker’s shot firing into the side-netting, before a wasted Townsend opportunity with the England winger finding the gloves of Roberts from 12 yards out.
But the attacker grabbed the winner with five minutes remaining, cutting in from the left and firing home a sweet effort into the top corner after Holtby broke on the counter.
Spurs first half (4-2-3-1): Friedel; Naughton, Kaboul, Veljkovic, Davies; Capoue, Mason; Eriksen, Lamela, Lennon; Soldado.
Spurs second half (4-2-3-1): Friedel; Walker, Dawson, Fryers, Rose; Carroll, Holtby; Townsend, Ceballos, Falque; Kane. Unused subs: McGee, Fredericks.