Nigeria forward, Taiwo Awoniyi, was involved as Nottingham Forest beat Chelsea 1-0 at Stamford Bridge on Saturday.
Awoniyi who has scored for Forest in all their Premier League matches this season already, set Anthony Elanga up to slot the only goal of the match home.
Chelsea’s spending on deadline day took their total splashed on new players in just over a year under a consortium fronted by Todd Boehly to over £1 billion ($1.3 billion).
Moises Caicedo’s move from Brighton which could rise to £115 million broke the British transfer record last month.
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But the Ecuador international was at fault for the only goal at Stamford Bridge to leave Mauricio Pochettino’s men embarrassed.
Elanga slotted home three minutes into the second half after Caicedo gave the ball away inside his own half.
New signing Cole Palmer was thrown on to try and turn the game around, but Chelsea’s lack of a natural goalscorer, despite their huge outlay, was again exposed.
Pochettino has won just one of his first four games in charge to leave Chelsea already eight points adrift of City.
Son shines for Spurs
Meanwhile, Son Heung-min’s netted three times in Tottenham’s 5-2 victory at Burnley on Saturday.
Spurs sit just two points behind City as their sparkling start under Ange Postecoglou continued.
Burnley had taken the lead after just four minutes at Turf Moor through Lyle Foster.
But Son, who was moved into a more central role by Postecoglou in place of Richarlison, soon proved his manager had pulled off another masterstroke.
The Tottenham captain’s deft chip levelled before a thunderous strike from Cristian Romero put the visitors in front in first-half stoppage time.
James Maddison’s curling finish from the edge of the box made it 3-1 before Son took centre stage to score twice in three minutes to complete his hat-trick.
Bournemouth were denied their first win under Andoni Iraola as Bryan Mbuemo snatched a 2-2 draw for Brentford.
Sheffield United and Everton secured their first point of the season after a pulsating 2-2 draw in the lunchtime kick-off.
Cameron Archer’s debut strike and a Jordan Pickford own goal put the Blades in front after Abdoulaye Doucoure’s early opener for Everton.
Arnaut Danjuma levelled early in the second half, but Everton needed some heroics from Pickford in stoppage time to prevent slipping to a fourth straight defeat.