The 1998-99 season may have ended in the most memorable fashion for Manchester United, but five months before securing an historic treble their domestic hopes were still far from certain. A defeat to Middlesbrough, coming on this day 17 years ago, left the Red Devils down in third place in the Premier League table and without a win in four games.
December really was a barren month for Sir Alex Ferguson and his men, as draws against Aston Villa, Tottenham Hotspur and Chelsea saw them slip up in a heated battle with arch-rivals Arsenal at the top. Things would become a lot clearer as the campaign wore on, with this shock 3-2 home reverse against Boro arguably providing the turning point in their campaign.
After this home loss, their first against the Smoggies since 1930, United would not lose another match in the top flight. A 20-game unbeaten run would prove to be enough to edge out Arsenal by a single point at the summit, while Champions League and FA Cup success provided Ferguson with the most impressive achievement of his illustrious Old Trafford tenure.
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It all seemed a far cry on this particular afternoon, however, as Boro extended their own impressive unbeaten run at the home of the eventual title winners in an impressive manner. The visitors were up and running 23 minutes in when Hamilton Ricard converted from close range on the back of a smart Brian Deane pass.
Gary Neville was at fault in the build-up to the opener, allowing Dean Gordon's cross to make its way to Deane, and it was Gordon who doubled his side's advantage eight minutes later when the full-back volleyed home Andy Townsend's half-cleared cross. Things may have seemed bad for the Red Devils at this stage, but matters were soon to get a lot worse when a third arrived before the hour mark.
Ricard and Dean were involved again, with the latter finding the net with his shot from the edge of the box following some more slack defending from the hosts. Three goals down and seemingly with little but pride left to play for, United finally found their groove and pulled one back through Nicky Butt's header to restore just a glimmer of hope.
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There was then just the one goal in it when, soon after being brought off the bench, Paul Scholes converted from the spot to leave Boro hanging on a little for the remainder at the Theatre of Dreams. Hang on they did, though, thanks to a big Mark Schwarzer save to deny Andy Cole just four minutes from time.
The full-time whistle marked a third defeat of the Premier League season for Fergie's men, but despite taking just three points from a possible 12 they were soon back on the winning trail. While Middlesbrough, promoted from the Championship the season prior, were happy to settle for a ninth-place finish, Man United more than redeemed themselves by lifting three trophies at home and in Europe come May.
In fact, redemption was the key word when the North-East outfit returned to Old Trafford the following month for an FA Cup third-round tie, which the Red Devils would win 3-1. That was the start of a strong run, taking in wins against Liverpool, Chelsea, Arsenal and indeed Newcastle United in the final along the way to their eventual success.
United would remain unbeaten in Europe all term, too, again beating the best of the best en route to lifting the trophy for just the second their in their history. It helped round off what is still arguably the finest campaign in the famous club's history, yet for those inside Old Trafford for the defeat to Middlesbrough, what would later transpire still looked a million miles away.
Manchester United XI: Schmeichel; G.Neville, Johnsen, Irwin, P.Neville (Solskjaer-78); Beckham (Scholes-64), Keane, Butt, Giggs; Cole, Sheringham
Middlesbrough XI: Schwarzer; Festa, Vickers, Cooper, Pallister, Gordon; Townsend, Mustoe (Moore-72), Maddison (Beck-83), Ricard; Deane