Tottenham Hotspur came from behind for the first time this season as they saw off a fatigued Southampton courtesy of a late Heung-Min Son penalty.
Danny Ings fired the hosts in front as he flicked on a header from an astute corner from James Ward Prowse.
Gareth Bale drew the hosts level with a cute curling finish before Son secured all three points for a struggling Spurs.
Story of the game
Spurs fans were unsure what to expect coming into this one. Daniel Levy had tarnished the reputation of the north London club in the recent days after the fiasco that was the European Super League.
The circumstances were not helped by the sacking of Head Coach Jose Mourinho two days ago, who had failed to beat any of the top 8 teams in the second half of the season.
Spurs skipper Hugo Lloris was called into action less than two minutes into the game as Mohammed Salisu powered a header straight at the Frenchman from 6-yards, before Che Adams thundered a volley towards goal on the rebound, just for Lloris to somehow block it.
Southampton used this momentum to put in a truly terrific first-half performance. Further shots from Ings, Theo Walcott, and Nathan Tella were unable to find the net.
Spurs had a good chance in the latter stages of the first half, as a ball found its way across the Saints box falling to Lucas Moura. But the Brazillian snatched at the ball and sent it over the bar.
Interim manager Ryan Mason must have finally got through to the players as they emerged for the second half a completely different team.
Gareth Bale, returning to the starting lineup for the first time since the defeat to Arsenal, had looked most likely to make something happen for Spurs, and he did exactly that in the 60th minute.
Some excellent play led to Lucas Moura having a shot at goal blocked, which fell to Bale, who shifted onto his left foot, before curling past a scrambling Alex McCarthy into the far corner.
Clearly fatigued from their FA Cup Semi-Final loss to Leicester City at the weekend, Southampton were struggling to stay in the game, especially since they had lost Ings to injury.
Spurs were really bringing the game to their visitors from the south coast, and they thought they had taken the lead when Son slotted a ball across from Sergio Reguilon past McCarthy.
However, Lucas Moura was judged to be offside and blocking the view of the Southampton goalkeeper, with VAR ruling out the goal.
Thankfully for Spurs fans, they were awarded a penalty in the 90th minute, as drama ensued.
A Son corner was seemingly cleared by the arm of Adams, and the following clearance blocked by the hands of center-half Toby Alderweireld. Whilst either of these instances could have been deemed a handball, it was Moussa Djenepo who went in late on Reguilon, which resulted in the penalty.
Referee David Coote originally gave the foul outside the box, but following an investigation by VAR, the foul was adjudged to be on the line of the penalty box, which prompted him to change the decision.
Son took on the responsibility for the penalty and sent McCarthy the other way, giving Spurs the lead for the first time in the match.
The Lilywhites were able to hold out for the remaining six minutes of stoppage time, to secure a big three points for Ryan Mason's men.
Spurs now sit two points of West Ham United and Chelsea, who face each other at the weekend, keeping their Champions League dream very much alive.
Southampton remain nine points off the relegation places and looks safe for another season.
Man of the Match - Gareth Bale
For someone who has been overlooked for the majority of Jose Mourinho's remaining days, the Welshman looked sharp and eager to cement his place in this Sunday's Carabao Cup final. A goal alongside some excellent transition play on a day in which Spurs needed someone to step on in the absence of Harry Kane, warrants the Man of the Match award.
Can Spurs end the drought?
Undoubtedly Mason will have had an eye on Wembley on Sunday. Spurs players have now had their opportunity to lobby for their place in the starting lineup.
Should they do the unthinkable and win their first trophy in 13 years, it would be extremely interesting to analyse the reaction of those around the club, including the fans. All would certainly be ecstatic to end the trophy drought. But, would they be willing to forget the actions of those at the top of the hierarchy in the last few days.