Wanderers’ Checkatrade Trophy group campaign began with defeat as they went down by two goals to nil at home to Everton on Tuesday night.
The deadlock was broken halfway through the first period with Calum Dyson unleashing a thunderous effort from distance which Mark Howard was given no chance with.
The visitors then doubled their advantage with just 12 minutes left, Conor McAleny powering home a header from a corner kick to put the result beyond doubt for David Unsworth’s side.
There were a number of changes for Wanderers in their starting XI, with Josh Vela taking the captaincy in the absence of Jay Spearing who took his place on the bench.
Youngsters Jack Earing and Alex Perry meanwhile were handed their first senior starts for the club.
The game got underway at Macron Stadium, although the opening stages of the encounter were fairly tentative as both sides looked to settle into the game.
The visitors however, despite their tender years, certainly weren’t just there to make up the numbers with Wanderers being forced to hold off pressure from the Toffees inside the opening ten minutes of the game.
Neither goalkeeper was being tested early on though, while the first change of the game arrived in the 20th minute with Jamie Proctor being replaced by Conor Wilkinson.
The deadlock was broken however just two minutes later with Dyson unleashing a sensational strike into the top corner of the net from all of 25 yards to give the Toffees the lead.
The visitors almost handed Bolton an equaliser shortly after though, with Bassala Sambou seeing his header pushed onto the post by Everton keeper Mateusz Hewlt.
As the half wore on though, it was Wanderers who were seeing more of the ball and with David Unsworth’s side being forced back in their numbers for sustained periods of play.
Chris Taylor meanwhile attempted to elude Hewelt in the Everton goal with eight minutes of the half remaining, only to see his free-kick from 20 yards fall kindly for the shot-stopper while Kaiyne Woolery saw his half volley from ten yards blocked at the death.
Those opportunities proved to be the last of the first half though as the half time whistle was blown.
With no changes at the break, proceedings got back underway as night time began to fall at Macron Stadium.
And the first chance of the half fell to Andrew Taylor, but the full-back’s volley flew high and wide of the mark in the 50th minute.
Wilkinson almost provided the perfect assist three minutes later, powering down the left flank before whipping a cross into the box which unfortunately nobody could connect with.
It was more Wanderers game inside the opening stages of the second period, with Wilkinson nodding a Chris Taylor cross just wide shortly after.
Woolery was proving Bolton’s main outlet of attacks, with the pacey forward proving himself a handful for the Everton backline.
With 22 minutes remaining, the manager made a double substitution with Gary Madine and Spearing being thrown into the mix for the final quarter of the game.
It was very much all Bolton as the clock ran down, with Wilkinson seeing his tame effort from the edge of the box fail to trouble Hewelt.
Out of nowhere however, the visitors doubled their lead in the 78th minute through McAleny who thundered a header into the net from a corner kick.
Wanderers almost halved the deficit straight away, but substitute Madine couldn’t keep his shot down after collecting a clever downfield ball.
Woolery then left the Toffees' backline panicking with his pace, eventually seeing his angled drive fly narrowly wide of the far post in the 88th minute.
Try as they might however, Bolton couldn't breach the Everton backline as the game was brought to its conclusion with the Goodison Park side running out winners.