The game could have been so different if the Addicks had taken some of the gilt edged chances that came their way before the interval.
Pritchard, Hulse and Cort could have netted and they were made to pay by a clinical Boro side after the break.
The Addicks were the architects of their own downfall in many ways, individual errors costing them dear. They slipped perilously close to the relegation zone and a stunned Valley knows things have to change quickly.
Cedric Evina’s knee injury left Chris Powell without a recognised senior left-back. Salim Kerkar stepped into the breach and Pritchard and Dervite were paired in the engine room. Powell reverted to a 4-4-2 starting formation with Bradley Wright-Phillips joining Hulse at the front. Stephens and Haynes were included amongst the substitutes.
The Addicks sustained another serious looking injury when Lawrie Wilson had to be withdrawn at half-time.
Johnnie Jackson talked Kerkar through the early stages of is new role, Kerkar’s energy presumably being the reason for him dropping back.
Pritchard started brightly and had an early chance to open his league account but he failed to hit the target with a header. Charlton soon made amends with a quick break after 12 minutes. Pritchard played the ball right to Rob Hulse who thundered home from the edge of the area.
A free-kick on the right gave gave Grant Leadbitter the opportunity to float a ball in for Jonathan Woodgate to head in the equaliser. Woodgate was given the freedom of The Valley to pick his spot.
The pivitol moment was the injury to Wilson. Dervite and Pritchard were holding their own in the middle of the park but Powell opted to switch Pritchard to the right and bring Dale Stephens on in the centre. Danny Green, a specialist right sided player, was left on the bench. If a right-winger is not used when the player in his position is injured, it is difficult to fathom why he was on the bench in the first place.
Inside the opening ten minutes of the second half, Boro took the lead. A mistake by Michael Morrison allowed on loan Chelsea youngster, Josh McEachran, to slip in Scott McDonald to fire home. Nine minutes later, the visitors effectively sealed the game when a booming clearance from keeper, Jason Steele, gave Ledesma the chance to lob Hamer.
Powell utilised various shapes, 3-5-2 and even 2-5-3 for a while as he tried to change the course of the game but to no avail.
Substitute, Richard Smallwood, added the fourth in stoppage time and even then, Boro had a golden opportunity to extend the margin.
By the end the Addicks’ wafer thin confidence had evaporated and too many heads went down.
These are worrying times at The Valley and questions are understandably being asked of the manager. He has had shocking luck with injuries but has also failed to make the best use of his squad on occasions.
Individual errors were a major factor in the defeat but it seems Powell is not only unsure of his best team but also of what system to use.
Table-topping Cardiff arrive at The Valley on Tuesday so Powell has to rally his troops quickly. He will also need to make a few phone calls to bring in a couple of new faces to freshen things up. If the Bluebirds join a growing list of clubs to take three points away from SE7, the Addicks could well slip into the bottom three and the board may feel they have to make a change at the helm.
Charlton: Hamer; Solly, Cort (Haynes 76), Morrison, Kerkar; Wilson (Stephens 46), Dervite, Pritchard, Jackson; Hulse, Wright-Phillips (Cook 76).
Subs (not used): Button, Taylor, Hollands, Green.
Goal: Hulse 12.
Booked: Pritchard 72 (foul).
Middlesbrough: Steele; Parnaby, Bikey, Woodgate, Friend; Haroun (Hoyte 90), Leadbitter, McEachran (Smallwood 90), Bailey; Ledesma (Jutkiewicz 67); McDonald.
Subs (not used): Leutwiler, Zemmama, Halliday, Reach.
Goals: Woodgate 27, McDonald 54, Ledesma 64, Smallwood 90.
Booked: Friend 39 (foul), Woodgate 41 (handball)
Referee: Graham Scott (Oxfordshire).
Attn: 17,744 (1,694 Middlesbrough).