At a lifeless Stade Louis II stadium, the home side grabbed an equaliser through Stephan El Shaarawy, who headed in Nabil Dirar's brilliant cross.
Nacer Chadli struck a shot narrowly over the bar in the first half, before Erik Lamela gave Tottenham the lead by finishing off a slick team move.
Harry Kane could have grabbed a second but had a low shot and header saved.
Tottenham are unbeaten in Group J after a win over Azerbaijani side Qarabag in their opening match.
Against Monaco, they looked like coasting to the three points after controlling most of the game, before two substitutes combined nine minutes from time to claim a point the hosts did not deserve.
After an exciting start to the season for Spurs, Dele Alli was given his first England call-up earlier in the day, and the 19-year-old showed his credentials with another eye-catching performance.
The former MK Dons man is strong enough to handle the physical side of the game and, despite his age, showed maturity in dealing with his defensive responsibilities. He worked hard to win back the ball, as well as making a crucial block on the edge of the area in the first half.
Offensively, his crisp forward passing and neat footwork put Tottenham on the front foot on numerous occasions, but most impressive was his composure in the opposition penalty area.
It led to the opener as he turned a Monaco defender before seeing his shot saved, with Lamela on hand to tap into an open net. Striker Kane was also a beneficiary of his good work but he could not find the back of the net.
Alli's all-action style may just provide the drive Roy Hodgson needs in England's central midfield, reminiscent at times of former Liverpool midfielder Steven Gerrard in the early part of his career.
It has taken a while, and it is still early in the season, but Argentine midfielder Lamela looks like he is finally beginning to repay the club record £30m fee that Spurs paid Roma in 2013.
He pulled the strings for Tottenham in their Premier League victory over Manchester City on Saturday and was impressive in the 65 minutes he was on the field in Monaco.
His graceful touch and ability to carry the ball has never been in question, but there is an end product to his game now. He started and finished the move for Tottenham's goal and has now netted three times and provided two assists in his past five games.
Lamela's performance was made easier by the time and space the hosts gave Spurs, but the visitors lost their focal point once he went off.
Monaco, who saw over £100m worth of talent depart in the transfer window including Anthony Martial to Manchester United, created little until a well-worked leveller that will leave Spurs boss Mauricio Pochettino frustrated.
Tottenham midfielder Dele Alli: "It was a strong first half and we could have seen the game out. It feels like a loss and we are down but we will pick ourselves up."
On his England call-up: "I was speechless. It has been a really good start to the season for me and I maybe didn't expect it to go this well."
Tottenham boss Mauricio Pochettino: "We are disappointed and it is two points lost. We could have been more clinical, I am happy with the display and effort.
"I am very happy for Dele. It is important to look after him. We have a great relationship with England manager Roy Hodgson and his staff."
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