Clinical Coventry scored four times to send struggling Barnsley to a seventh straight league defeat for the first time since 1959.
The Reds bravely battled away in the second half - which will have been some comfort to under pressure manager Lee Johnso, but remain in the League One drop zone after this latest reverse.
Two down at the interval, prospects for the Reds - and possibly Johnson’s job - looked bleak, but the visitors scored three times in the second period as they gave it a real go against a side who look every inch automatic promotion-chasers.
Johnson’s Reds could scarcely have got off to a worse start as the mist and rain descended on the Ricoh Arena.
After just three minutes they conceded, with young Liverpool loanee Ryan Kent lashing home his first senior goal, right-footed across recalled goalkeeper Adam Davies after he had skipped easily past defender Marc Roberts.
It was a disastrous start and skipper Alfie Mawson tried his best to bring about a swift response, but his free-kick from 25 yards drifted harmlessly over the top.
The Reds were plunged further into trouble after 17 minutes when the Sky Blues - flying high in League One under experienced boss Tony Mowbray - doubled their lead in clinical fashion.
This time full-back Aaron Phillips crossed in superbly for Newcastle loanee Adam Armstrong, who crashed home first time from close range to register his 11th goal of the season.
Prospects at that point were bleak, though to their credit, the Reds players didn’t let their heads drop.
They probed, albeit with precious little success, though Lewin Nyatanga saw a header drift wide from Gorge Smith’s cross.
Ben Pearson’s fiercely-struck free-kick was deflected wide for a corner-kick, but things weren’t quite happening for Johnson’s men once again.
Former England star Joe Cole - on loan at the Sky Blues from Aston Villa - fired an effort off target, while John Fleck tested Davies as the hosts ended the first period very much on top.
There was early second half encouragement for the Reds when Pearson fizzed a long-distance strike inches wide after just 25 seconds.
Encouragement then turned to joy three minutes later when Johnson’s men halved the deficit at the start of an amazing four-goal blitz.
Mawson headed home Josh Scowen’s corner-kick to make it 2-1 in the 48th minute, before Armstrong rapidly restored the hosts’ two-goal advantage when he smashed past Davies after meeting ex-Red Jim O’Brien’s pass.
Scowen’s crisp finish made the score 3-2 in the 54th minute, seemingly giving the Reds fresh hope, only for ex-World Cup star Cole to strike again to make it 4-2, and the game was still only in the 60th minute.
Former Chelsea and West Ham man Cole certainly showed his class, smashing a superbly-struck free-kick in off the underside of the crossbar.
The Reds continued to plug away, and they almost clawed back another goal when Mawson saw a header hacked off the line by Coventry ‘keeper Rhys Charles-Cook.
Scowen incredibly made it 4-3 from the penalty spot deep into stoppage-time, but while it wasn’t quite enough, there were plenty of positives to focus on in this latest defeat.
Coventry: Charles-Cook, Phillips, Ricketts, Martin, Stokes, Vincelot, Fleck, Kent (Tudgay 70), Cole (Murphy 62), O’Brien (Lameiras 62), Armstrong.
Subs not used: Burge, Haynes, C Thomas, Fortune.
Yellow cards: None
Red cards: None.
Barnsley: Davies, Roberts, Mawson, Nyatanga, Wabara, Scowen, Pearson, Isgrove, G Smith, M Smith (Wilkinson 60), Winnall (Jackson 84).
Subs not used: Townsend, Bree, Abbott, Maris, Templeton.
Yellow cards: Wabara (12), Mawson (59), Wilkinson (82).
Red cards: None.
Referee: Michael Bull (Essex).
Star man: Ben Pearson.