Wanderers crashed out of the FA Youth Cup following a 3-2 defeat against Accrington Stanley at the Wham Stadium.
Lamine Toure scored twice for the Whites but Aaron Pickles and a brace from Leslie Adekoya saw the hosts progress to the third round.
Bolton nearly took an early lead when Noah Halford headed into the side netting after getting on the end of Max Conway’s inviting cross.
Jack Dallimore then made a fine stop to tip Calvin Harper’s effort over the bar after Bolton were caught out by a long ball.
The Whites went in front through Toure, who tapped home after Louis Hood had spilled Matthew Tweedley’s strike from distance.
At the other end, Dallimore made another smart stop to keep out Harper’s thumping strike from the edge of the box.
After the break, Adekoya got Accrington back on level terms after a moment to forget for Dallimore, who failed to hold onto Harper’s shot.
And the Reds took the lead when Adekoya smashed home from close range after a dangerous attack down the right wing.
The Whites had an immediate reply as Toure gave Hood no chance with a ruthless strike after the hosts had failed to deal with Joel Burgess’ cross.
But Accrington went back in front moments later when Pickles provided a simple finish after Dallimore had made a fine stop to keep out Devonport’s header.
The hosts went down to 10 men when Harvey Monk was shown a straight red for hauling down Mitch Henry.
And Henry went agonisingly close to an equaliser on the stroke of full time, sending an effort just wide of the post.
Accrington: Hood, Akukwe, O'Brien (c), Gough (Kardacz), Pickles, Monk, Devonport, Harper (Lawton), Adekoya, Trickett, Poilly
Unused Subs: Clayton, Henderson, Newton, Procter, Eze
Bolton: Dallimore, Burgess (Pinto), Conway, Halford, Kamara, Sharples, Henry, Tweedley (c), Toure (Shakespear), Pettifer, Wilcox (Frimpong)
Unused subs: Maher, Inwood, Beardsworth, Fleury