Jacob Maddox netted two as Cheltenham Town beat Arsenal U21’s 6-2 in the Checkatrade trophy fixture at the Jonny Rocks Stadium.
Chris Clements got the opener with a fantastic free-kick and Will Boyle, Kelsey Mooney and Ryan Broom were also on the scoresheet in Michael Duff’s first win for Cheltenham.
Arsenal U21’s goals came from Tyreece John-Jules and a penalty from Charlie Gilmour.
Freddie Ljungberg’s side played at least 83 minutes with 10 men after Robbie Burton was dismissed for a late challenge.
The win sees Cheltenham go second in group 13.
The Robins were lining up against a side that hadn’t lost since August, where Manchester City U23’s beat them 6-5.
It was Michael Duff’s side that had the first chance of the night when a poor clearance found Jacob Maddox wide open in front of goal, but Iliev saved his effort at goal.
Then came Arsenal’s red card, just seven minutes into the game, midfielder Robbie Burton’s challenge was late and saw him sent for an early bath.
From the resulting free kick Chris Clements thumped the ball into the top right-hand corner to put the Robins 1-0 up.
Cheltenham then began to dominate the chances, next up was Kelsey Mooney, a great flick from McAlinden in the box found the young striker, but his tame effort was well met by Iliev.
Arsenal started to come back into the game shortly after creating their first shooting opportunity. A cross from the right found Trae Coyle who’s backheeled effort was blocked before it could trouble Scott Flinders.
The Arsenal defence seemed rather slow to start as another mistake between the back line and goalkeeper Iliev ended up in Kelsey Mooney having an effort blocked off the line after latching onto the loose pass.
Jacob Maddox was next to fire a shot towards Iliev, another mix up by Arsenal, Maddox took the ball on and struck one from the edge of the box, but his effort went over the bar.
Cheltenham continued to move forward, Maddox again getting involved, feeding Kelsey Mooney. Mooney was one on one with Iliev but the Arsenal goalkeeper made a good save.
Arsenal’s response came from some good running by Bukayo Saka. He was fouled after getting to the edge of the Cheltenham’s box, Ben Sheaf struck the resulting freekick well, but it went just wide of Flinders left post.
Cheltenham’s next chance was there next goal. Sean Long with a superb bit of play down the right-hand side, his cross was perfect for Will Boyle who had stayed up after a free kick, Boyle made no mistake in heading past Iliev.
Arsenal came back immediately, Tyreece John-Jules made his way onto a through ball, rounded Scott Flinders and slotted home.
Arsenal certainly found their footing in the game, their movement and quick passing began to cause Cheltenham problems as John-Jules found himself in front of goal for his second, but he couldn’t get a shot away after a good turn.
Cheltenham began the second half well, their first shot was their third goal, Jacob Maddox getting on the end of a Liam McAlinden cross to slot home 3 mins after the restart.
Jacob Maddox then netted again in the 51st minute, Ryan Broom’s cross found the youngsters head and he cushioned it past Iliev, with a slight deflection off an Arsenal defender.
Cheltenham’s two goals at the start of the second half gave them a comfortable three goal advantage, as the second half wore on their man advantage showed, they played a lot of football in the Arsenal half.
Then in the 65th minute Arsenal got a penalty, John Jules causing problems again, Scott Flinders tripped the forward. Charlie Gilmour stepped up and scored the spot kick, striking well to Flinders right.
Both sides continued to battle well, both exchanging long range efforts which went well over the bar.
Alex Addai had the next chance, he did well to take on the Arsenal left back, he fired one across goal towards the top corner, forcing a brilliant save from Iliev.
Kelsey Mooney then smashed in Cheltenham’s fifth of the game in the 84th minute. A simple pass found him just outside the box and he thumped home.
The Robins last attack of the game was then Ryan Broom’s goal, he hit the ball into the roof of the net to round off a brilliant performance by the Robins and give Michael Duff his first win as manager.
CHELTENHAM TOWN (4-4-2): Flinders; Boyle, Forster, Tozer; Field , Long (Broom 45), Thomas (Atangana 54), Maddox (Addai 70), Clements; McAlinden, Mooney; Subs not used:Mullins, Lovett, Barnett, Varney
ARSENAL UNDER-21s (4-3-3): Iliev; ballard, Bola (Zelalem 63), Medley (Bramall 90), Sheaf (smith 28); Burton, Gilmour, Coyle, Olayinka, saka; John-Jules; Subs not used: Thompson, Tormey, Balogun, Hein
REFEREE: A Martin
ATTENDANCE: 1,431 (431 from Arsenal)
Report by George Didcote