Charlton's relegation worries deepened as Middlesbrough came from behind for their first away win of the season.
Cattermole (second from right) is congratulated for scoring Boro's equaliser
Ex-Boro striker Jimmy Floyd Hasselbaink put the hosts ahead when his shot deflected off Jonathan Woodgate and looped over Mark Schwarzer.
Lee Cattermole equalised when he slotted home just before the break after being set up by Mark Viduka.
Julio Arca side-footed Boro ahead in the 63rd minute before Yakubu sealed the win with a sweet right-footed shot.
In the absence of top scorer Darren Bent, Charlton's front pairing of Marcus Bent and Hasselbaink put the visitors' defence under pressure and it needed the calming influence of Jonathan Woodgate to keep them in check.
And their intentions were made clear early on when Hasselbaink was booked for a nasty follow-through on former team-mate George Boeteng.
Yakubu nearly broke the deadlock at the other end when he glanced Cattermole's cross from the right straight into the arms of on-loan goalkeeper Scott Carson, back in the side after being ineligible for last weekend's 2-0 FA Cup humiliation at Nottingham Forest.
But the Addicks deservedly took the lead in the 27th minute thanks to a slice of good fortune.
A long ball up field rebounded off the back of Emanuel Pogatetz and Hasselbaink's deflected shot looped off Woodgate and over the stranded Schwarzer for the Dutchman's fourth goal in 20 Charlton appearances.
Boro had gone into the game as one of four clubs still searching for their first away top-flight win of season, having previously picked up just four points out of 33 on their travels.
Boro's Mark Viduka holds off Charlton skipper Matt Holland
Their last win on the road came at Manchester City on 2 April but they were given hope when they equalised on the brink of half-time.
Viduka dinked a delicate pass in for Cattermole to drill home only his second Middlesbrough goal, although Charlton were furious as Andy Reid appeared to be fouled when dispossessed in the build-up.
Just as Charlton looked to be stepping up for a second-half charge, Arca hit them with a sucker punch when he swept home from 10 yards after 63 minutes.
And the game was effectively over three minutes later when Yakubu's swerving drive from the left deceived Carson and flew home from 16 yards.
Matt Holland's fierce drive needed to be turned around the post by the sprawling Schwarzer but by then Charlton had run out of ideas.
This win for Boro, adding to their 3-1 home win over Sheffield United on New Year's Day, was their first back-to-back three-pointer in 13 Premiership outings.
And on Gareth Southgate's 25th game in charge, it opened up an 11-point gap between themselves and their relegation-haunted hosts.
Charlton, whose 2-0 reversal at the Riverside in December proved to be former manager Les Reed's last in charge, had gone into the game boasting the leakiest defence in the division.
And despite a promising first half, new boss Alan Pardew saw again that defensive frailties are costing his new side dearly as they slumped to their fifth home defeat of the season.
Charlton manager Alan Pardew:
"We gave an honest account of ourselves but it wasn't enough today.
"The third goal really killed us off, coming so quickly after the second, and with that cushion, Middlesbrough were able to pass the ball well and control the game.
"We had to play at full throttle if we were going to win and I thought for 62 minutes we did.
"But you could sense that when the second went in a little bit of spirit went out of us and after that they immediately followed that up with a wonder goal which just knocked the suffing out of us."
Middlesbrough boss Gareth Southgate:
"This first away win was long over due.
"At the start, we were a bit passive and trying to win this in first gear, but as soon as we attacked, you could see their anxiety and it was crucial to get the equaliser just before half-time.
"We had to weather a bit of a storm at the start of the second half, but after we got the two quick goals, that finished the game."
"It is nice to get that monkey off our backs. Now we have climbed a couple of places and I hope we can build from this."
Charlton: Carson, El Karkouri, Diawara, Hreidarsson, Thatcher, Rommedahl (Thomas 83), Holland, Reid, Ambrose (Hughes 83), Marcus Bent (Sam 74), Hasselbaink.
Subs Not Used: Randolph, Faye.
Booked: Hasselbaink, Holland, Ambrose.
Goal: Hasselbaink 27.
Middlesbrough: Schwarzer, Xavier, Woodgate, Pogatetz, Taylor, Cattermole, Boateng (Morrison 74), Arca, Downing, Viduka (Euell 90), Yakubu (Christie 83).
Subs Not Used: Jones, Davies.
Goals: Cattermole 45, Arca 63, Yakubu 68.
Ref: M Dean (Wirral).