They went out of the FA Cup, had Stephen Clemence sent off, but, far worse in terms of preserving their Premiership status, Jurgen Klinsmann was carried off the pitch with a broken jaw.
The injury happened 10 minutes from time when the German rose for a challenge with Arjan de Zeeuw. Both players were knocked off balance and as Klinsmann fell his head caught the Barnsley defender's shin. He was carried off and taken to Barnsley District Hospital.
A spokesman for the hospital said: "It has been confirmed that Mr Klinsmann has broken his jaw. He will remain in hospital overnight for observation. His condition is satisfactory."
Tottenham's physiotherapist, Tony Lenahan, was staying overnight at the hospital with Klinsmann.
The replay was won and lost in the second half and there was little doubt as to the turning point. Tottenham had played the prettier football for most of the evening and they appeared to be gathering momentum as they monopolised possession on the re-start until Clemence's dismissal after 49 minutes stopped them in their tracks.
The 19-year-old had been cautioned in the first half for a foul on Nicky Eaden and when the referee, Gerald Ashby, adjudged he had dived over a challenge by Adie Moses in an attempt to get a penalty, a second booking and red card was the only option.
With that the match swung resolutely in the home side's direction. Within a minute Ashley Ward had put them ahead and Neil Redfearn and Darren Barnard also scored to make David Ginola's 72nd-minute goal direct from a free-kick a flamboyant irrelevance. Barnsley now travel to Manchester United in the fifth round.
It was a harsh outcome for Ginola, who had a marvellous match. Barnsley's manager, Danny Wilson, had pinpointed the Frenchman as the potential danger and he lit up the night with some glorious passing and running. The nearest he came to scoring in the first half, however, arrived in the 22nd minute when his near-post shot from Ruel Fox's cross appeared destined for the net until Dave Watson made a magnificent save, diving to his right.
It did not appear so then, but it would prove to be the closest Tottenham would come to winning the tie. With the visitors still sorting themselves after Clemence's dismissal, Barnsley advanced down the left and Redfearn's cross was met at the near post by Ward, whose fierce header shot past Baardsen.
After 58 minutes it was 2-0 and again it was an attack on the rebound. First Fox had an effort cleared off the line by Chris Morgan, then Martin Bullock countered with a charge through the middle. His first attempt was blocked and when he tried a second time, his mis-hit fell to Refearn, who shot through a crowd of players into the net.
That was it we thought, and Barnsley certainly gave the impression they believed the tie was over as they squandered chance after chance by attempting to walk the ball into the net. But with over-elaboration becoming the theme, Ginola proved the exception with the direct approach.
Morgan fouled Ramon Vega, for which he was booked, and from a range of 25 yards the Frenchman curled a delightful free-kick with his right foot over Watson's dive and into the top corner of the net.
That heralded a furious finale that only subsided when Klinsmann was injured. Tottenham pressed forward, Barnsley counter-attacked and the latter proved to be decisive in the 88th minute when Bullock and Redfearn teed up Barnard on the left apex of the area. A ferocious shot speared into the roof of a net for a goal worthy of deciding any cup tie.
Sadly for Tottenham, the match might have more serious implications for their season.
Barnsley (3-5-2): Watson; De Zeeuw, Moses, Morgan; Eaden, Bullock, Bosancic, Redfearn, Barnard; Hendrie, Ward. Substitutes not used: Liddell, Tinkler, Hristov, Markstedt, Leese (gk).
Tottenham Hotspur (4-4-2): Baardsen; Carr, Vega, Campbell, Wilson (Howells, 57); Fox, Berti (Armstrong, 67), Clemence, Ginola; Ferdinand, Klinsmann (Brady, 80). Substitutes not used: Calderwood, Brown (gk).
Referee: G Ashby (Worcester).Reuse content