Wanderers' Under-18s were knocked out of the FA Youth Cup at the third round stage after goals in each half saw them lose 2-0 to Middlesbrough on Thursday night.
Starting slowly at the Riverside, the young Whites fell behind midway through the first half as Stephen Walker powered home.
Dennis Politic went close on a number of occasions as Nicky Spooner's side looked to force an equaliser but Tyrone O'Neill's cool finish sealed their fate.
Bolton found themselves under pressure straight from kick off with James Aspinall first called into action inside the opening two minutes to deny Bilal Brahimi when one-on-one.
The hosts had a deflected effort ruled out for offside soon after, while Luca Navarro dragged narrowly wide as the Trotters created their first opening after 15 minutes.
Middlesbrough took the lead after 24 minutes as Walker went on a mazy run into the Wanderers penalty area before powering home into the roof of the net from an acute angle.
Aspinall showed good hands to deny Layton Watt from distance just before the half-hour mark.
The young Whites finished the half strongly as they went in search of an equaliser, but to no avail with Luca Connell and Edward Brown both seeing efforts blocked before Politic forced goalkeeper Zach Hemming into a fine save at his near post.
Brown and Politic continued to threaten for Bolton with the former turning well on the edge of the box before firing straight at Hemming and then coming within a whisker of converting a corner at the far post, while the latter fired narrowly wide with another long-range strike on the stroke of half-time.
The Trotters continued to look lively after the break as captain Matthew Fearnley saw a powerful effort from distance palmed away, while Politic caught Hemming out with a fizzing effort across goal only to see it fly just wide of the far post.
However, Middlesbrough remained a threat themselves with Brahimi missing a golden chance to double the Teessiders' lead, side-stepping his marker before leathering over from close-range.
At the other end, Hemming denied Politic from distance once again with Navarro seeing his follow-up blocked.
The young Whites had the woodwork to thank for not falling further behind midway through the half as O'Neill saw his rising strike bounce down off the crossbar, onto the post and away.
As the game passed the 70-minute mark, the game was decided in the space of 60 seconds with big chances as both ends.
Having seen Fearnly place a first-time strike narrowly wide after running onto Navarro's blocked effort, Bolton were made to rue their previous missed opportunities as O'Neill made no mistake when given a second sight of goal.
Springing the offside trap, the foward finished coolly with the outside of his foot into the bottom corner to double his side's lead and consign the Trotters to a third round exit.
Wanderers kept fighting until the last kick however, with Politic seeing a diving header kept out by Hemming and Fearnley going close once again.
But it was not to be as the young Whites' FA Youth Cup exploits came to a premature end at the Riverside.
Bolton: Aspinall, Moulden, Edmondson (Hartshorne 67), Jones-Griffiths, Broughton, Boon, Politic, Connell, Brown (Moore 67), Fearnley, Navarro (Argent-Barnes 81).
Unused subs: Darcy, James.