Three years after winning promotion, and then being denied top flight football for financial irregularities, the Robins finally reached the elite after 73 years of trying thanks to a pulsating 4–3 win over Leicester City in the Division One playoff final. The only downside to this superb triumph was the departure of player-manager Glenn Hoddle to Chelsea. His assistant John Gorman was left behind to pick up the pieces, and it took 16 games for Swindon to record their first top division win.
Swindon never adjusted to the pace of Premiership football, winning just five games and becoming the first top division team in 30 years to concede 100 league goals. They would have fared worse still had it not been for the strong form of Norwegian striker Jan Åge Fjørtoft, who was on target 12 times in the league.
They did not achieve a win in the league until their 16th game, finally achieving their first ever top flight victory on 24 November 1993 when a Keith Scott goal gave them a 1-0 home win over Queen's Park Rangers. Their 20th game of the season was a memorable one. They travelled to Anfield to face Liverpool, and managed to hold the home side to a 2-2 draw just over three months after they had crushed Swindon 5-0 at the County Ground. Midfielder John Moncur had put Swindon 1-0 up on the hour, and although Liverpool equalised after 71 minutes, Swindon restored their lead three minutes later with a goal from Keith Scott. They were still ahead with five minutes remaining, before an 86th minute equaliser from Liverpool's Mark Wright denied Swindon a famous victory. Swindon won their next game 2-1 at home to Southampton. They held Sheffield Wednesday to a thrilling 3-3 draw at Hillsborough on 29 December with two goals from striker Craig Maskell. However, after the turn of the new year, Swindon found themselves on the receiving end of some more heavy defeats. On 15 January, they lost 6-2 to Everton at Goodison Park, though they did manage a narrow victory over Tottenham Hotspur in their next game, and within a month had fallen to a 5-0 defeat at Aston Villa. They were then crushed 7-1 at Newcastle on 12 March. A 2-2 home draw with Manchester United on 19 March sparked hopes that Swindon could climb to safety, but they collected just two points from their final eight games and were firmly rooted in bottom place.
John Gorman spoke of his hope that Swindon would soon return to the Premiership, saying that "[Swindon] wouldn't be in Division One for long . . . "