Coventry City 4 (Kent 3, Armstrong 18, 52, Cole 60)
Reds 3 (Mawson 48, Scowen 54, 90+4 pen)
A rollercoaster of a second half saw the Reds come close to earning a positive result after a good second period, but former England international and three-time Premier League winner Joe Cole put the game beyond doubt to secure a 4-3 victory for Coventry at the Ricoh Arena.
A late Josh Scowen penalty did give the Reds some deserved respectability as far as the scoreline was concerned in what was a much-improved display from the Reds.
With the Reds after a positive start, they got off to a terrible one. It seemed Reece Wabara had made a great clearance with a header but was then caught out of position, with Kent steaming in to meet Fleck's nod into the channel. After running at Roberts, he cut inside before bending into the far corner from just inside the area.
Barnsley's first sniff of goal came from a 30-yard free-kick on 10 minutes that Alfie Mawson cracked well over the crossbar.
It seemed luck wasn't on Barnsley's side as a clearance from Nyatanga was blocked into the path of Armstrong for a free run at goal. Thankfully, Adam Davies made a very smart save low to his left to keep out the vicious effort on 15 minutes.
Coventry made it look so easy on 18 minutes as they doubled the lead. Kent had the freedom of the right flank and his pull-back was expertly despatched by Armstrong from 15 yards.
With half-an-hour gone, the Reds started to ease their way into the match with time on the ball but failed to carve any real chance for Smith or Winnall up top.
Just before the break, Ben Pearson almost embarrassed Ricketts as he nearly nicked the ball from a pass back to Charles-Cook but the 'keeper managed to gather just as Pearson got a foot on the ball.
Within 30 seconds of the restart, Ben Pearson registered two shots on goal for the Reds - one straight from kick-off and a second more meaningful effort after a surging run that saw his shot zip just wide.
On 48 minutes Barnsley were back in the match. Josh Scowen whipped in a brilliant corner which Alfie Mawson rose highest to meet and power a header home.
The goal had breathed some life into the Reds, although Adam Davies had to beat away a powerful Armstrong drive as Coventry countered well.
Barnsley's sniff of hope was quickly taken away as Adam Armstrong raced clear with ease once again - duly despatching when one-on-one with Davies on 52 minutes.
However, Josh Scowen hit back again for the Reds with a well-taken goal just two minutes after the hosts' third. He did well to win a header before bearing down on goal and sending the ball across the 'keeper.
Conor Wilkinson was introduced just a minute before the hour, seconds after Mawson had upended Armstrong 25 yards out. Joe Cole punished the Reds, curling into the top corner for a goal on his debut.
It was almost 4-3 on 63 minutes when Marc Roberts' missile of a throw was flicked on by Mawson but Charles-Cook did well to tip away just on the line.
A gilt-edged chance was blazed by Conor Wilkinson after an inch-perfect through-ball from Pearson found the forward's clever run but he thumped wide from 15 yards.
Barnsley built up a head of steam but the ball simply wouldn't drop in the area. Pearson and Smith pumped some dangerous balls in for Wilkinson and Winnall, but nothing would drop for the Reds in the box.
Only two minutes remained when Alfie Mawson, Barnsley's man of the match, saw an effort cleared from the line after Charles-Cook flapped at a deep cross but Mawson's looped attempt lacked the necessary power.
Davies made two saves in stoppage time from Murphy and Tudgay - the former's attempt forcing the better of the two saves made by the Reds' 'keeper.
In the fourth minute of stoppage time, Simeon Jackson forced Phillips into a handball in his own area resulting in a penalty for the Reds. Josh Scowen took responsibility and sent the 'keeper the wrong way but it was just too late for the Reds to force another attack.
Coventry City: Charles-Cook, Phillips, Martin, Ricketts, Stokes, Vincelot, Fleck, O'Brien (Lameiras 61), Kent (Tudgay 70), Cole (Murphy 61), Armstrong.
Subs: Burge, Haynes, C. Thomas, Lameiras, Fortune.
Reds: Davies, Smith, Wabara, Roberts, Nyatanga, Mawson, Pearson, Scowen, Winnall (Jackson 84), Isgrove, M. Smith (Wilkinson 59).
Subs: Townsend, Bree, Abbott, Maris, Templeton.
Referee: Michael Bull.