Under-fire Robbie Fowler shrugged off his nightmare run on and off the pitch to put Liverpool one step away from a return to Wembley.
The England striker - hounded and abused after claims that he wanted ?50,000 a week to stay at Anfield - lifted his personal gloom by netting the winner in this Coca-Cola Cup semi-final first leg.
For long spells it looked as if Middlesbrough would take a draw back to the Riverside Stadium for the second leg on February 18, after Jamie Redknapp had cancelled out Paul Merson's opener for Boro.
But Fowler, with just one goal in his six previous games, has been writing his own headlines throughout a goal-laden career and he produced a winner in the dying minutes to silence his critics.
Middlesbrough had done their level best to halt the red tide and Liverpool were reduced to impotence for long spells.
Steve Vickers and Nigel Pearson were solid, patrolling Fowler closely for long spells, while 18-year-old Stevie Baker was detailed to follow every move Steve McManaman made.
He took on the thankless task with great determination and was never more than a few inches from the England star, tugging and pulling at him.
The tenacity shown by Baker summed up the Boro effort and in the early stages they showed a capacity to break with pace.
From one move a Merson freekick was headed wide at the far post by Neil Maddison.
Michael Owen, with a glorious turn and run, flashed a 20-yarder wide andthen the Liverpool boy-wonder set up Paul Ince for a near-post shot that was held low down by Mark Schwarzer.
But Liverpool had started poorly and their scrappy play was punished in the 28th minute, when Andy Townsend fed Craig Hignett in midfield and the ex-Crewe star clipped a superb ball into the path of Merson.
Liverpool were caught out, with Dominic Matteo playing Merson onside, and the England striker strode on to lash a low drive past an exposed David James.
Middlesbrough's legion of fans were still in mid-celebration when Redknapp levelled the scores.
He took a square ball from Owen and smashed a stunning 25-yard drive high into the roof of the Boro net with Schwarzer clutching thin air.
Matteo was booked for bringing down Merson, despite the former Arsenal man's pleading with referee Gary Willard to be lenient.
Vladimir Kinder and then Baker - for stupidly flicking the ball away after conceding a freekick - were next to see yellow. Phil Babb soon followed for dragging back Mikkel Beck.
After Redknapp's equaliser Middlesbrough were not too bothered about pacy breaks, but more concerned with deep, blanket defence as Liverpool's attacks washed around them.
Steve Harkness and Jason McAteer from distance, and then Oyvind Leonhardsen from inside the six-yard box, after McManaman and Owen had created havoc, threatened the breakthrough.
Fowler had a glorious chance on 70 minutes, when Owen spun on the left to fire over a cross, but the struggling hitman volleyed wide as he raced in unmarked at the far post.
Seconds later Owen almost punished Pearson when a Redknapp pass bounced off the big defender into the teenager's path, but the resulting 20-yarder dipped over.
Karlheinz Riedle came on with 15 minutes to go in place of Harkness, Roy Evans resisting the temptation to drag Fowler off and save him any further mental punishment.
The Kop started to take pity rather than criticise when Fowler rose unchallenged eight yards out, but only managed to plant his header wide.
The Liverpool fans behind the goal rose as one to encourage Fowler as he hung his head - and nine minutes from time they got their reward.
Owen showed pace and a fine shimmy to get away from Vickers on the right of the box, and when the low cross flashed into the six-yard box, Fowler wasthere to volley it home.
Liverpool: James, McAteer, Babb, McManaman, Leonhardsen, Fowler, Redknapp, Harkness (Riedle 76), Ince, Owen, Matteo.
Subs Not Used: Carragher, Friedel.
Booked: Matteo, Babb, Ince, Riedle.
Goals: Redknapp 31, Fowler 82.
Middlesbrough: Schwarzer, Maddison, Kinder, Vickers, Pearson, Mustoe, Hignett (Harrison 78), Townsend, Beck, Merson, Baker.
Subs Not Used: Moreno, Campbell.
Booked: Kinder, Baker.
Goals: Merson 29.
Ref: G S Willard (Worthing).
Copyright - Press Association