Goals from Robbie Keane and Jermain Defoe set up a grandstand finish after we'd trailed 3-2 but the equaliser proved elusive despite just about camping in Charlton's box for the last half-hour.
We had numerous efforts at goal in the last few minutes before the final chance fell at the feet of Defoe in injury time only for Matt Holland to get across and deflect his shot wide.
The first half was a cat and mouse affair until Charlton opened the scoring on 16 minutes. It followed their best spell of pressure as Shaun Bartlett guided home Jerome Thomas' cross from the left.
Keane and Fredi Kanoute went close but Charlton doubled their lead on the break after 38 minutes when ex-Spur Luke Young crossed deep for the diving Bartlett to head home.
An uphill task at half-time looked like an impossible one just four minutes into the second half when Thomas played a one-two with Bartlett only for his shot to clip off Ledley King and beyond the helpless Paul Robinson.
There were signs that we could get back into it when Kanoute's drive cannoned back off the foot of the post and Michael Carrick's arrival also seemed to add some drive from midfield - he soon set up Defoe who shot wide.
The game changed again after 67 minutes. Kiely spilled a high ball under pressure, Reto Ziegler battled for the loose ball and his second attempt was goalbound before Bartlett handled off the line. Bartlett was sent off, Keane buried the penalty, 3-1, 10 men, game on.
We needed a second goal quickly and it arrived 12 minute later. Keane's persistence after losing possession won the all back, he fed Defoe who spun to finish superbly into the corner from 12 yards.
It was now one-way traffic with Charlton defending deeper and deeper and Robinson starting attacks from midway in our half.
Keane, Ziegler, Carrick and King twice all tried their luck before that final chance fell to Defoe only for Holland to keep the points safe.
GUIDE TO THE ACTION
1min: Redknapp first shot of game, speculative effort from 30 yards that ended up in Row X.
8mins: Good cross from Pamarot from right flank, Keane dummied, Kanoute effort blocked.
12mins: Mendes played in Defoe over the top, right channel, waited for support but overhit cross.
16mins: Charlton's first serious spell of pressure, Thomas dinked in cross from left, Bartlett guided home on volley from eight yards.
Spurs 0, Charlton 1
34mins: Quick free-kick, Keane floated cross to far post, glancing header from King just wide.
37mins: Decent possession, Mendes nodded into danger area as Charlton pushed out, Kanoute onside, tricky angle, blasted over.
38mins: GOAL. Charlton break, Kishishev down the line to Young, deep cross headed home by Bartlett from six yards.
Spurs 0, Charlton 2
40mins: Defoe brought down on edge of box, took free-kick himself into wall.
44mins: PENALTY? Appeals for penalty for shirt-pulling on Keane waved away.
Injury time: Robinson out quickly to slide and gather as Young threatened to latch onto Murphy's pass.
Half-time: Spurs 0, Charlton 2
Half-time: SUB. Ziegler for Davies.
46mins: Holland dragged shot wide from 22 yards.
46mins: Ziegler volleyed high and wide from 25 yards.
48mins: King header from Keane free-kick no trouble for Kiely.
49mins: GOAL. Thomas one-two with Bartlett on edge of box, shot deflected off King, left Robinson helpless.
Spurs 0, Charlton 3
53mins: SAVE. Good work from Ziegler, inside to Keane, shifted onto his right foot, low drive from 12 yards but Kiely held on well.
54mins: WOODWORK. Kanoute sweet drive from 25 yards struck inside of post with Kiely beaten and bounced to safety.
59mins: SUB. Carrick for Redknapp.
60mins: Carrick straight into it, strode away from two challenges and played ball into Defoe who shot over under pressure.
65mins: Bunjevcevic effort deflected into air but Kiely under it safely.
67mins: PENALTY/RED CARD/GOAL. Scramble in Charlton's area after Kiely spilled high ball, Ziegler onto it, first effort blocked, second on target only for Bartlett to dive and palm off line. Bartlett sent off. Keane drilled penalty past Kiely, who guessed right.
Spurs 1, Charlton 3
75mins: Naybet header from Keane's deep corner always going over.
76mins: YELLOW. Thomas for studs up on Pamarot.
77mins: Mendes fired over after clearance from free-kick fell to him 30 yards out.
77mins: Keane thunderbolt blocked by Perry.
79mins: GOAL. Move broke down, Keane won ball back and fed Defoe who smashed home on the turn from 12 yards.
Spurs 2, Charlton 3
80mins: SUB. Euell for Johansson.
81mins: Kiely almost spilled Keane bouncing volley from 20 yards.
84mins: MISS. Euell clean through but clearly offside, drew Robinson but lifted ball wide.
84mins: SUB. Konchesky for Thomas.
85mins: Ziegler effort straight at Kiely as Charlton are rattled.
86mins: Carrick difficult volley flew into stand.
88mins: PENALTY? Naybet bundled over but nothing really there.
88mins: SUB. Fortune for Murphy.
89mins: King headed over from Keane's cross.
Injury time: Robinson deep free-kick, Kanoute flicked on, Defoe inches away as the ball skidded just wide.
Injury time: YELLOW. Young for dissent.
Injury time: CHANCE. Mendes cross fell to Defoe, shooting chance but magnificent block from Holland.
Full-time: Spurs 2, Charlton 3
Line-ups: Spurs (4-4-2): Robinson; Pamarot, King, Naybet, Bunjevcevic; Davies (Ziegler, 45), Mendes, Redknapp (Carrick, 59), Keane; Kanoute, Defoe. Subs: Keller, Brown, Edson Silva Sousa.
Charlton: Kiely, Young, Perry, El Karkouri, Hreidarsson, Kishishev, Holland, Murphy (Fortune, 88), Thomas (Konchesky, 84), Johansson (Euell, 80), Bartlett. Subs: Jeffers, Andersen.
Referee: Neale Barry.
A thrilling late comeback wasn't enough as Charlton took the Premiership points at the Lane on Saturday.