Luke Woolfenden netted a header and Kundai Benyu (pictured) a brilliant freekick but Town’s U23s were defeated 4-2 by Charlton Athletic at Playford Road, with stunning second-half strikes from Reeco Hackett-Fairchild and Josh Umerah securing the Addicks victory, Umerah and Mikhail Kennedy having scored the visitors' earlier goals.
Neither side threatened until the 17th minute when Ben Morris deftly took down Chris Smith’s excellent pass down the left but Charlton keeper Dillon Phillips did well to cut out the Blues’ striker’s low cross.
But from the resultant corner Woolfenden, playing at right wing-back with Town lining-up in a 3-5-2 system with Smith and George Fowler either side of Paul Digby, put the Blues in front.
Benyu whipped the ball over from the left and Woolfenden’s header back across goal went through a crowd of players before hitting the net.
However, the Town lead lasted until only the 21st minute when, after the Blues had failed to clear, the ball fell to Umerah, who hit a shot on the turn which flew through keeper Harry Wright’s legs.
Woolfenden almost scored what would have been a goal virtually identical to his earlier header in the 27th minute when again found at the far post by Benyu’s corner. But this time the defender nodded over.
Six minutes later Joe Aribo hit a shot through a crowd of players which Wright batted away.
The Addicks had been the better side but without creating many opportunities but on 39 they went in front. Archie Edwards crossed from the left and Kennedy forced the ball over the line from close range, Blues defender Smith perhaps getting the final touch.
Town immediately switched to four men at the back with Digby moving into a central midfield holding role and Benyu to the left.
Just before the break Town claimed a penalty when another dangerous Benyu corner from the left appeared to be turned behind by a Charlton defender’s hand ahead of Smith at the far post. The referee waved away Blues' protests.
Nine minutes after the restart Benyu got Town back on terms after Adam McDonnell had been fouled three yards outside the area. The 18-year-old grabbed the ball and then delicately curled the ball to keeper Phillips’s left and into the top corner of the net.
💥💥💥 BANG! @kundaibenyu_ scored this screamer of a free-kick for Town's U23 side earlier today #itfc
All the goals to follow soon âš½ pic.twitter.com/vWHiW689jz– Ipswich Town FC (@Official_ITFC) November 14, 2016
Charlton almost hit back immediately again but Wright did well to block from Kennedy at close range as he sought to add the final touch to Hackett-Fairchild’s ball in from the left. Soon after, Conor McKendry replaced Flynn Downes in the Blues midfield.
The Addicks were close to going back in front on the hour when Wright made a double save from Regan Charles-Cook and Umerah before Fowler cleared the latter’s subsequent effort off the line.
But the visitors only had to wait a minute more for their third of the afternoon, and what a goal it was. Hackett-Fairchild took the ball inside his man on the Charlton right and hit a powerful shot which beat Wright to his left.
McDonnell headed Woolfenden’s cross from the left to Addicks keeper soon afterwards but on 66 Umerah sealed the three points for the South Londoners with a goal even better than Benyu and Hackett-Fairchild’s earlier strikes.
The powerfully-built frontman rolled his marker and from 30 yards out lashed an unstoppable shot beyond Wright and into the net.
The Blues looked to get back in the game but Myles Kenlock scuffed weakly to the keeper on 71 after Digby had found him with a crossfield ball.
Seven minutes later Hackett-Fairchild wasn’t too far away from his side's fifth with a freekick which he curled just past Wright’s left post.
In the final 10 minutes McKendry shot over after a freekick had been cleared to him just outside the box, then curled an effort into the arms of Phillips.
The scoreline was a fair reflection of the game with the visitors having been the better side for the most part, while the Blues played some decent stuff at times.
Benyu’s excellent goal and dangerous set pieces, from which Woolfenden scored his goal and might have grabbed a second, were the highlights for Town, while Charlton’s two second-half strikes were also worthy of a much bigger stage.
Manager Mick McCarthy and his assistant Terry Connor were among those watching Gerard Nash’s side.
Meanwhile, U23s coach Nash will be taking the 2016/18 FAI UEFA Pro Licence coaching course over the next 18 months, along with ex-Blues loanee Keith Andrews among others.
Town’s U18s, who won 4-1 at QPR on Saturday with Kieron Cathline, Pat Webber, Conor McKendry and Bailey Clements netting the goals, are in action on Tuesday night in their Suffolk Premier Cup quarter-final against a Leiston first team at Victory Road (KO 7.45pm), having defeated Kirkley and Pakefield 5-1 in the first round.
Ryman League Premier Division Leiston defeated the Town youngsters 6-2 at the first round stage of the competition last season.
U23s: Wright, Woolfenden, Kenlock, C Smith, Fowler, Digby, Benyu, Downes (McKendry 58), Morris, McLoughlin, McDonnell. Unused: Hayes, Cathline, Folami, Webber.