The captains, officials and mascots line up before United v Middlesbrough in December 1998

#Treble99: The last time we lost in an epic season

If there was a price to pay for the dizzying highs which would punctuate the end of the 1998/99 season, then much of it was settled by the home defeat to Middlesbrough - on this day in 1998.

Alex Ferguson's United would not taste defeat again all season – little wonder after the bitter taste which lingered long after Bryan Robson’s side had plundered three easily avoidable goals and extended the Reds’ winless run to six games.

“The entertainment is glorious, it is just the results that are a problem,” wrote Guy Hodgson, of the Independent. Worryingly, Alex Ferguson’s men had won only twice in the last ten games and for an hour of this match were too easily outplayed.

Boro deserved their first win at Old Trafford since 1930, racing into a three-goal lead inside 60 minutes before a late United fightback almost pilfered an undeserved share of the spoils. For the Reds, it was a study in absence; with Alex Ferguson away due to a family bereavement and Jaap Stam nursing an ankle injury.

Striker Hamilton Ricard signalled that he was attuned to the occasion with an early blockbuster which required a fingertip save from Peter Schmeichel, and the Colombian opened the scoring in the 23rd minute with a simple tap-in after both Gary Neville and Schmeichel might have intercepted Dean Gordon’s cross or Brian Deane’s pull-back respectively.

Robson brought his side to Old Trafford on the back of a 10-game unbeaten run, and lurking just four points behind United. The Reds legend had identified a weakness in United’s defence at set-pieces, which was spectacularly exposed after the half-hour as Gordon doubled United’s deficit.

The excellent Andy Townsend picked out Deane with a cross-field free-kick and, though Ronny Johnsen was able to head clear, the Norwegian failed to do anything other than tee up Gordon for a thunderous, first-time volley across Schmeichel and into the bottom corner. Old Trafford’s frustration turned to stunned silence, the annoyance of again missing a chance to move top of the table made way for genuine concern about the unfolding nightmare.

United limped in and out of the interval with little change in their fortunes, with no way to be found through the Boro defence, spectacularly marshalled by former home favourite Gary Pallister, back at Old Trafford for the first time since his summer transfer to Teesside.

The difference between the two sides was highlighted in the visitors’ third goal, which stemmed from a fine Steve Vickers interception to snuff out a half-chance for Andy Cole.

Though Boro lost the ball to Johnsen deep inside his own half, the Norwegian’s inexplicably slack pass infield to Gary Neville only found Ricard. The striker’s pass for Deane was too heavy, but ricocheted off Phil Neville and back into the Deane’s stride and, to cap off a horrific concession, the ensuing shot was saveable by Schmeichel’s standards, but merely squirmed under the Dane’s grasp and rolled into the Stretford End goal.

With half an hour to go, finally United were awoken, quite possibly by the mirth of the away supporters, who were singing ‘We’re gonna win the league’ as Nicky Butt leapt to head home a fine, deep cross from David Beckham.

Paul Scholes replaced Beckham, who had been booked, and caretaker manager Jim Ryan’s move soon paid off, as a goalmouth melee culminated in the substitute sliding in to prod a finish past Mark Schwarzer. Just over 20 minutes remaining and, somehow, it was game on.

Boro, to their credit, rode out the storm, with their five-man defence coping admirably with a forward line now comprising Cole, Teddy Sheringham and Ole Gunnar Solskjaer. The former almost saved the day, pouncing on Schwarzer’s slack pass to Pallister and charging through on goal, but the Australian recovered to take the sting out of Cole’s shot and Vickers cleared to preserve his side’s victory.

With one win in nine and a porous defence shipping goals, United’s situation looked far from rosy. Fortunately, the afternoon would prove a launchpad from which the Reds would scale new heights.

Teddy Sheringham of United and Middlesbrough's Gary Pallister.
Former Reds defender Gary Pallister was victorious on his return to Old Trafford with Middlesbrough.

MATCH DETAILS

Saturday 19 December 1998 | Premiership | Old Trafford | Attendance: 55,152

MANCHESTER UNITED 2 (Butt 62, Scholes 70)
MIDDLESBROUGH 3 (Ricard 24, Gordon 31, Deane 59)

United: Schmeichel; P.Neville (Solskjaer 79), Johnsen, G.Neville, Irwin; Beckham (Scholes 64), Keane, Butt, Giggs; Sheringham, Cole.

Subs not used: van der Gouw, Blomqvist, Brown

Booked: Beckham

Middlesbrough: Schwarzer; Festa, Cooper, Vickers, Pallister, Gordon; Mustoe (Moore 72), Maddison (Beck 83), Townsend; Deane, Ricard.

Subs not used: Roberts, Blackmore, Stockdale

Booked: Festa

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