Middlesbrough manager Steve McClaren's troubled times show no sign of relenting as his side again face an FA Cup replay.
For a man being touted as possible successor to Sven-Goran Eriksson in the England hotseat, despite a very public display in signing a new four-year contract, McClaren cannot buy a win these days.
After a wretched first-half display, Jimmy Floyd Hasselbaink fired the visitors into a lead, against the run of play, 29 seconds after the restart.
But a dominant Coventry deservedly earned a fourth-round return to the Riverside courtesy of a sweet strike from Stern John.
Unlike three weeks ago when Boro were surprisingly held to a 1-1 draw at non-league Nuneaton in the third round - just nine miles away in this part of the Midlands they must now loathe - there was no awful surface to impede McClaren's side.
Instead, the Ricoh Arena offered the highly-paid Boro stars all the comforts of a stadium fit for the Premiership, and one of the best looking pitches in professional football.
For the opening two minutes Boro were lively and enterprising, but from such bright beginnings their first-half performance descended into a dour affair.
Instead, they were forced to dig in as Coventry proceeded to control matters, enjoying a considerable amount of possession as they found themselves encamped for long periods in the Boro half.
This was no scratch Boro side either, despite McClaren making five changes to the team beaten in the final minute by Wigan last week at The Riverside.
Mark Schwarzer returned in goal for his first game since January 2 after coming off the transfer list, and in the fairness to the Australian, he had little to do in the first half.
McClaren's side were at least defensively sound after coming into the game having conceded 15 goals in their five matches this month.
That was despite losing Ugo Ehiogu with a knee injury in the 28th minute, the centre-back only returning last week after five weeks out in the wake of his on-off move to West Brom.
But after Schwarzer was tested by a low 25-yard left-foot drive from the sparkling Gary McSheffrey in the third minute, the Sky Blues struggled to find the pass to unlock the visitors.
John had two bites of the cherry in the 27th minute, but failed to savour either, with his initial effort blocked, and when the ball eventually returned to the striker, a left-foot effort flew past the angle of bar and post.
After Lee Cattermole was fortunate not to be penalised for clipping McSheffrey in the area seven minutes from the break, referee Chris Foy unmoved, Dele Adebola then scuffed an effort a yard wide of the left-hand post from just inside the area.
So much, though, for apparently galvanising words in the Boro camp throughout the week, with McClaren confirming management and players had spoken of the current malaise and how best to emerge from it.
Instead, there must have been a half-time rocket from McClaren as his side swiftly broke the deadlock at the start of the second half.
Coventry simply went to sleep at the back as a flick from Aiyegbeni Yakubu found a wide-open Hasselbaink to volley home his seventh goal of the season, and second in successive games.
Two minutes later and it could have been 2-0 as a well-worked free-kick move led to a Yakubu strike from 15 yards that was pounced upon by Marton Fulop, who had not touched the ball in the first half.
But Coventry were unfazed and by the 54th minute were back on level terms, primarily due to the industry of McSheffrey.
Chasing what appeared to be a lost cause, McSheffrey managed to hook a loose ball to the edge of the area from the bye-line.
He was ultimately rewarded for his efforts, initially with Ehiogu's replacement in Matthew Bates failing to clear the awkward, bouncing ball.
That allowed Don Hutchison to nod the ball on to John to strike a sweet volley from 12 yards for his fourth of the season, all in the last six matches.
Yakubu and Adebola traded chances soon after, but from that moment City again dominated, with McSheffrey in particular terrorising Boro on the left, overshadowing England's left-wing star Stewart Downing.
But despite the best efforts of Micky Adams' side, as Boro creaked and groaned under the weight of City pressure, they failed to find the winner they richly deserved.
Teams:
Coventry Fulop, Duffy, Shaw, Williams, Hall, Scowcroft, Doyle,Hutchison (Jorgensen 86), McSheffrey (Impey 90), Adebola,John (Morrell 90).
Subs Not Used: Page, Ince.
Goals: John 54.
Middlesbrough Schwarzer, Parnaby, Ehiogu (Bates 28),Southgate, Pogatetz, Mendieta, Cattermole,Rochemback (Doriva 72), Downing, Hasselbaink,Yakubu (Viduka 65).
Subs Not Used: Knight, Johnson.
Booked: Bates.
Goals: Hasselbaink 46.
Att: 28,120
Ref: C Foy (Merseyside).