Wanderers came from behind to beat Crewe Alexandra at Gresty Road on Wednesday evening and in turn, book their place in the second round of the Carabao Cup.
The hosts drew first blood in the clash with three minutes of the first half remaining, with Chris Porter nodding home from close range.
The Whites were level with 19 minutes to go however, with Adam Armstrong notching his first in Bolton colours when slotting home from six yards out following superb link-up play between Antonee Robinson and Will Buckley.
And with the stage set, up stepped Derik Osede with his first goal for the club with just eight minutes left - an effort which proved to be the winner come full-time.
There were ten changes for Wanderers from the side who started against Leeds United on Sunday, with Stephen Darby the only figure to remain from that XI.
There was a combative feel to proceedings as the game got underway, with both sides clearly up for the cup clash.
And Wanderers looked dangerous on the counter, with Antonee Robinson and unusually Derik causing problems in Crewe’s penalty area.
Both sets of fans were responding to the bright start with their backing, while the home side themselves saw a number of lofted balls into the box plucked to safety by Ben Alnwick.
Chris Dagnall in particular was looking a threat for the Railwaymen, with his quick-footed runs into the area ensuring that the Bolton defence were on their guard.
As the game headed towards its half-hour mark however, neither side had troubled their respective goalkeepers.
With 31 minutes gone however, Will Buckley looked set to tee up one of his advancing teammates when cutting inside and lifting the ball across goal when reaching the byline, but a Crewe body somehow managed to get in the way and force it out for a corner-kick.
That was without doubt Bolton’s best chance of the game so far, although Tom Lowery’s superb outswinging cross and Porter’s consequent header ensured that the Alex responded with a glorious chance of their own.
Buoyed by their close-opportunity, Dagnall also came within inches of opening the scoring, only to see his header fall kindly for Alnwick between the sticks.
They were eventually rewarded for their efforts three minutes before the break however, with Porter nodding home at the far post.
And although it was virtually all Bolton for the final stages of the first half, they couldn’t force a quick-fire equaliser and went in at the break a goal down.
With no changes for either side, the second half got underway as the sun was setting at Gresty Road.
And it was the home side who started the brighter, with Wanderers penned into their own box for the opening stages of the final 45.
They were struggling to get any real sight of goal however against a dogged Bolton backline, with Porter's lofted effort from 25 yards out failing to hit the target.
The 978 travelling Bolton fans were still making themselves heard though, with their backing filtering through to the players who were finding their feet in the clash.
Crewe were standing firm however and were certainly making life difficult for the Whites as they looked for a route back into the game.
And they almost had a second in the 64th minute as Alnwick somehow palmed away Porter's point-blank range header from a deflected cross into the six-yard box, while Brad Walker's daisy-cutter was inches wide of the upright moments later.
With 24 minutes remaining, Wanderers made a statement of intent with a triple substitution of Gary Madine, Filipe Morais and Jem Karacan.
Their job was almost made twice as hard just moments later though as Porter saw a lofted shot cannon off the crossbar, much to Bolton's relief.
On the counter attack however, Wanderers were level in the 71st minute with Armstrong slotting home from close range after collecting Buckley's cross.
And the comeback was completed in the 82nd minute as Derik nodded home Morais' free-kick to the delight of the travelling faithful.
With the clock running down to full-time, Crewe threw men into the mix in a bid to force an equaliser and with it, extra time.
And with the game hitting the 90 minute mark and three minutes of additional time indicated, there was no let-up from the home side.
But try as they might, they just couldn't find a way past Phil Parkinson's side as the Whites marched into the second round of the competition.