The match was preceded by a minute’s applause for Bolton midfielder Fabrice Muamba, who suffered a cardiac arrest on the pitch in the original tie.
And on an emotional night, visiting goalkeeper Adam Bogdan was in superb form before being beaten three times in the final 20 minutes of the game.
The Trotters were on the back foot in the first half but man-of-the-match Bogdan was in determined mood and produced a superb double save to foil first Jake Livermore and then Luka Modric.
The Hungarian went on to push Emmanuel Adebayor’s shot away and block Gareth Bale’s follow-up before capping a fantastic half with a tremendous one-handed stop after Scott Parker had latched onto Bale’s pass.
Spurs continued to press after the break, Rafael van der vaart hitting the crossbar with a delightful whipped free-kick, and Bogdan was soon back in the thick of the action, pulling off fine saves when Van der Vaart and then Adebayor were put through on goal.
But his brave resistance finally ended when he failed to claim a Van der Vaart corner and Ryan Nelsen (74) was on hand to head home at the back post.
Spurs added to their lead three minutes later after a swift counter-attack ended with Jermaine Defoe playing in Bale, who calmly steered his shot past Bogdan.
Bolton pulled one back in the final minute, substitute Kevin Davies arriving at the back post to convert Ivan Klasnic’s right-wing cross, but Spurs had the final say with the last kick of the game, substitute Louis Saha curling a delightful shot into the corner from just outside the penalty area.