Teenager Alex Henderson scored his first senior goal on his second start for Accrington Stanley but the Reds lost to League One Bolton Wanderers in the last 16 of the Bristol Street Motors Trophy.
The Trotters, chasing promotion to the Championship, went 2-0 up in the first half before Academy product Henderson struck.
The Reds pressed for an equaliser but a late Kyle Dempsey wonder strike secured holders Bolton the victory – it was Wanderers who knocked Stanley out in the semi-final of the competition last season.
Henderson came in for the injured Shaun Whalley with skipper Seamus Conneely also back for the suspended Ben Woods.
Jack Nolan had an early strike deflected wide and Stanley enjoyed a spell of pressure around the Bolton box.
However Wanderers took the lead on 15 minutes when a long ball forward was flicked on, Joe Gubbins headed it back towards goal but Cameron Jerome rushed onto the loose ball and he chipped it over the outrushing Joe Walsh.
Stanley then forced the pace, launching a number of corners into the Bolton box but were unable to test keeper Joel Coleman.
The League One side made it two on 29 minutes when they broke quickly and Conneely was judged to have fouled Paris Maghoma in the area. Although Walsh dived the right way, Aaron Morley found the far corner of the net.
Josh Woods fired straight at Coleman as Stanley looked to get back in it and they did on 37 minutes when Henderson pounced as Bolton failed to clear their lines, he nicked the ball and fired home from 25 yards to celebrate his first goal for the club in his breakthrough season.
Bolton almost replied immediately but Kyle Dempsey fired narrowly wide and Walsh did well to deny Jon Dadi Bodvarsson.
Dempsey rifled another over the bar and Luke Matheson’s close-range strike was high at the end of the first half.
After the break, QPR loan keeper Walsh dived low to keep out Will Forrester’s close-range header and Dempsey drilled the ball across the box with Matheson unable to get a touch at the far post.
At the other end, Joe Pritchard’s free kick was collected by Coleman and Nolan, rushing into the six-yard box, couldn’t convert a cross as the Reds looked for an equaliser.
Stanley kept pressing and Nolan had a fierce strike pushed out by Coleman and, from the resulting corner, Dan Martin blasted an effort narrowly wide.
Dempsey secured a quarter-final place for Bolton on 83 minutes when he got the ball on the left and ran to the edge of the area, rifling the ball into the back of the net, giving Walsh no chance.
Stanley: Walsh, Shipley, Gubbins, Hills, O’Brien, Martin, Conneely (McConville), Henderson, Pritchard, Nolan, J Woods
Subs: McIntyre, Mellor, McConville, Quirk, Pickles, Adekoya, Trickett
Crowd: 3441 (2346 from Bolton)
Yellow: Martin, J Woods, O’Brien, Hills