Spurs gave up three goals in regulation and they looked like a side that did not want to advance to the quarterfinals of the Europa League.
In extra time, Emmanuel Adebayor was able to score in the 96th minute to give the North London club the advantage on away goals.
Despite giving up a fourth goal in the 110th minute, Spurs were able to escape Northern Italy with a spot in the final eight.
Here are the complete set of player ratings for Tottenham from their horrific showing at the San Siro.
Player: Brad Friedel
Friedel cannot be blamed for the goals that Inter Milan scored at the San Siro on Thursday night.
The American international did let in three goals, but also made nine saves in the match to keep the Spurs alive in the Europa League.
Friedel also found his way into the book in the 44th minute because of time wasting.
Players: Kyle Walker, William Gallas, Jan Vertonghen, Kyle Naughton
Grades: Walker: 6; Gallas: 4; Vertonghen: 5.5; Naughton: 6.2
There are not many positive things to say about how the Tottenham back four performed at the San Siro.
Walker almost cost Spurs the match towards the end of the second half as his wild tackle completely missed Esteban Cambiasso.
Luckily for Walker, Cambiasso's shot went just wide of the post and Spurs were able to advance to extra time.
Gallas made plenty of mistakes on Thursday night and it is shocking that he was allowed to stay on the pitch for the entire match.
The Frenchman let Antonio Cassano get wide open on the first Inter goal and his deflection off of a free kick in the 75th minute resulted in an own goal.
Gallas had a chance to make amends for his mistake in the 94th minute, but his header failed to test Inter keeper Samir Handanovic.
Vertonghen was not immune to making mistakes either as he failed to mark Ricky Alvarez properly on the fourth Inter goal that was scored in the 110th minute.
Naughton was fairly quiet on Thursday night compared to his teammates in the back four. He did have a chance on goal in the 85th minute when he sent a screamer towards Handanovic.
Players: Gylfi Sigurdsson, Scott Parker, Jake Livermore, Moussa Dembele
Grades: Sigurdsson: 7; Parker: 6.5; Livermore: 6.2; Dembele: 7
Sigurdsson was one of the few bright spots in the Tottenham attack throughout the entire match. The 23-year-old won all of his aerial battles and he ended the match with a 91 percent pass accuracy.
Parker had the most touches of all the Tottenham players on Thursday night with 112, but he was unable to connect with the player alongside him in the center of the midfield until late in the second half.
Before Livermore was taken off in the 70th minute, he picked up a yellow card and he had very little impact on the final result of the match.
Dembele started out the match on the right wing in place of the injured Aaron Lennon. When Lennon eventually entered the match in the 70th minute, Dembele was able to shift into a more central role in the midfield.
In the 96th minute, Dembele was able to unleash a shot that resulted in the lone Tottenham goal, which was enough to earn them a spot in the quarterfinals.
Players: Jermain Defoe, Emmanuel Adebayor
Grades: Defoe: 5; Adebayor: 6.5
Once again, the forward partnership of Defoe and Adebayor was ineffective. The two forwards played together for 56 minutes before Defoe was taken off in favor of Lewis Holtby.
Defoe only had 27 touches and one shot during his 56 minutes on the pitch.
Once Defoe was taken out of the match, Adebayor was left as the lone forward in the lineup. In the 96th minute, Adebayor was able to force his way in between two Inter defenders and slot home the only Spurs goal of the match.
The abysmal showing by the pairing of Defoe and Adebayor once again proved that the best formation that Tottenham lines up in is the 4-2-3-1.
Players: Lewis Holtby, Aaron Lennon, Steven Caulker
Grades: Holtby: 6.5; Lennon: 6.5; Caulker: 6
Holtby was the first Tottenham substitute to make his way on to the pitch in the 56th minute and he was able to create a few chances in the Spurs' attack towards the end of the second half.
Lennon's introduction to the match in the 70th minute allowed Dembele to move into a more central position in the midfield.
In his time on the pitch, the English winger had 38 touches and was able to take one shot.
Caulker came on in the 104th minute as an extra center-back to help disrupt the Inter attack.
There was one goal scored by the Italian club during Caulker's time on the pitch, but he was not at fault for the 110th minute goal by Ricky Alvarez.
All statistics courtesy of WhoScored.com
Follow me on Twitter, @JTansey90.