If Barnsley were going to lose their unbeaten record anywhere this season it was probably always going to be at Coventry.
They simply hate visiting the Sky Blues and 95 years of misery was compounded when Jordan Willis' late header inflicted their first League One defeat of the season.
This was their 25th visit to either Highfield Road or the Ricoh Arena without a win, going way back to the opening day of the 1923-24 season when Peter Sant's side won 3-2.
So there really is no surprise that Daniel Stendel's attempt to become the Barnsley manager with the best ever league start to a reign fell flat in the West Midlands.
It could have been different as the Reds had enough chances to have taken something out of the game, though Stendel was far from happy with his side's generosity at the other end, particularly with the defending that allowed Willis to head home the winner from an 80th-minute free-kick.
“I think we gave Coventry too many chances to score,” Stendel accepted after the game.
“We also had big chances, but in all the games before we didn't give the opposition so many chances like today.
“That is for me the reason we lost and we didn't really defend together. But I think we had enough chances to get something.”
Jacob Brown, making his first league start for the club, had the best of those, especially in the first half when he latched on to a defensive mistake but then saw Lee Burge make a stunning save as the goalkeeper tipped his effort on to the post.
Burge was at it again after the break, producing a flying stop to keep out Mamadou Thiam's effort as Stendel's men chased that club record, but Coventry also had their chances.
Conor Chaplin, who Barnsley had spent all summer trying to sign from Portsmouth, put an effort just wide when through on the goal while Jonson Clarke-Harris also had a good opportunity.
In the end it was settled via a set-piece when Willis bravely crashed home a header from close range to give the Reds that familiar sinking feeling at Coventry.
There were positives to take from the afternoon. Other sides at the top also lost, as Peterborough and Walsall also saw their unbeaten records go.
Oh, and at least they do not have to go back to Coventry any time soon.
Coventry: Burge, Willis, Doyle, Chaplin, Hyam, Junior Brown, Sterling, Clarke-Harris, Bayliss, Thomas (Bakayoko 89), Shipley (Kelly 68).
Unused subs: O’Brien, Davies, Hiwula, Andreu, Thompson.
Barnsley: Davies, Cavare, Pinnock, Lindsay (McGeehan 82), Pinillos, Dougall, Bahre (Moncur 65), Mowatt, Thiam, Moore, Jacob Brown (Adeboyejo 72).
Unused subs: Walton, Bird, Jackson, Williams.
Referee: Trevor Kettle