Liverpool striker Neil Mellor grabbed a brace to knock holders Middlesbrough out of the Carling Cup.
Mellor (left) scored two late goals for Liverpool
Mellor got his first with a powerful left-foot strike during an end-to-end climax to the game.
Middlesbrough will feel aggrieved by the defeat as Boudewijn Zenden had a goal disallowed for offside while Joseph Desire Job also hit a post.
But Mellor made sure of the Liverpool win when he chipped in a Darren Potter through ball into the Boro box.
There was an impeccably observed minute's silence before the game to honour former Anfield great Emlyn Hughes who died on Tuesday.
And Reds midfielder Igor Biscan continued his rich vein of recent form as he impressed and he saw an early 25-yard shot saved.
Liverpool looked the more threatening and striker Florent Sinama-Pongolle saw a close range angled shot parried by keeper Nash.
Anfield hold's a minute's silence for Liverpool legend Emlyn Hughes
Stephen Warnock gathered the loose ball and crossed for Mellor only for the forward to head disappointingly over from six yards.
The game became a rather subdued affair, although Middlesbrough will feel they should have gone into the interval ahead.
Zenden put the ball in the net but his effort was ruled out for offside.
The home goal again came under threat and keeper Jerzy Dudek was forced into vital saves to keep out shots from Job and Viduka.
Nash was also proving tough to beat in the Middlesbrough goal and he did well to keep out a Warnock shot.
The attacking urgency increased as the match drew on with both sides seemingly keen to avoid extra time.
And Job hit the post for Boro with a 25-yard shot but it was Liverpool who took the lead when Mellor struck after 83 minutes.
The win was confirmed as Mellor also scored in the last minute as the visitors poured forward in search of an equaliser.
Liverpool: Dudek, Finnan, Henchoz, Whitbread, Traore, Potter,
Biscan, Diao (Welsh 75), Warnock (Riise 82),
Sinama Pongolle (Partridge 69), Mellor.
Subs Not Used: Luzi Bernardi, Raven.
Goals: Mellor 83, 89.
Middlesbrough: Nash, Davies, Cooper, Riggott, Queudrue,
Morrison (Graham 81), Doriva, Zenden, Downing, Job, Viduka.
Subs Not Used: Schwarzer, Boateng, Wilson, McMahon.
Ref: H Webb (S Yorkshire).