A late brace from substitute Mustapha Carayol subjected Blackpool to another defeat, as luck again deserted The Seasiders at Bloomfield Road.
There was little to choose between the pair before Carayol bent in an 84th minute opener after a quick Middlesbrough break.
The winger then fired a second into the top corner in added time to pile further misery on Paul Ince's out of form side.
Angel Martinez had the best of Blackpool's chances from long range, but Shay Given found himself largely untested throughout, as Pool's unhappy start to 2014 continued.
Ince named an unchanged side for the game, and his captain Barry Ferguson registered the first shot early on, firing at Given.
At the other end it took a fine goal-saving tackle by Craig Cathcart, on his 100th appearance for the club, to deny Lukas Jutkiewicz after 13 minutes.
Jack Robinson then produced a similar tackle to deny Boro's leading scorer Albert Adomah from opening his account.
Pool's start was a promising one, Ricardo Fuller was a menace to the Boro back line, heading over Robinson's long throw. Whilst Angel shot at Given soon after, but it was bread and butter for the former-Newcastle stopper.
Blackpool's Spaniard had the taste for it, next his exquisite volley was well held by Given. It meant, despite a positive first-half for the hosts, they went in for half-time level.
Half Time: Blackpool 0-0 Middlesbrough
After the break both sides attempted to gain the early advantage, first Thomas Ince had an effort blocked, before Rhys Williams suffered the same fate for Boro.
On the hour mark Blackpool lost Tom Barkhuizen, who was forced off through injury, with Nathan Eccleston his replacement.
It was the visitors who were inches away from leading however, when Emanuel Ledesma fired a free-kick onto the cross bar, before The Seasiders scrambled it to safety.
With little over ten minutes remaining Steve Davies replaced Fuller, as Ince freshened things up.
Soon after Neal Bishop's glancing header sparked another scramble, but luck wasn't on Pool's side. Basham then had a header cleared before Boro produced the sucker punch.
A quick breakaway saw Carayol run at the Blackpool defence, before bending an irresistible finish into the bottom corner to put the visitors ahead with six minutes remaining.
Blackpool's final throw of the dice was James Caton, who replaced Angel with five minutes left.
A late equaliser never looked likely for Pool, and Carayol added insult to injury, firing into the top corner after it broke to him inside the box, to seal his side's win.
Full Time: Blackpool 0-2 Middlesbrough
By Mark Ridgway