A goal in each half from Bristol City ensured that ten-man Wanderers slipped to defeat at Ashton Gate on Tuesday evening.
Following a fairly evenly contested first half, the deadlock was broken with seven minutes of the opening 45 remaining as Famara Diedhiou turned the ball home at the far post from a matter of yards out.
The Whites were also reduced to ten men on the stroke of half time as Filipe Morais was penalised for a second bookable offence.
The Robins then doubled their advantage with 13 minutes of the game to go, with Aden Flint's horribly deflected effort trickling into the net after wrong-footing Mark Howard to make sure of the points for the home side.
It was a debut for new signing Karl Henry, with the midfielder going straight into the Whites’ starting XI – one of six changes from the side who turned out against Brentford at the weekend.
There was also a first league start for Jeff King following on from his senior debut against West Ham in the Carabao Cup a week ago.
Proceedings got underway under the floodlights at Ashton Gate, and the game started in combative fashion with the home side forcing Bolton to stand firm early on.
And debutant Henry was called upon inside the opening four minutes as he cleared a dangerous Jamie Paterson cross away from the Whites’ six yard box.
Bailey Wright then tried his luck from the edge of the box, but his audacious volley failed to trouble Howard.
For all their possession in Wanderers’ half however, the home side weren’t causing too many problems in front of goal at the game reached its quarter-mark.
And Bolton even had a chance themselves, with Darren Pratley’s effort deflecting away for a goal-kick with Frank Fielding stranded.
The home side then enjoyed their best chance of the game, but Paterson wasn’t able to get the power needed behind his shot from eight yards and Howard comfortably gathered down to his left.
The Robins were looking a threat going forward however, with Andrew Taylor having to remain calm and collected with eight minutes of the half remaining to head a loose ball back to his goalkeeper.
And just a minute late, Diedhiou turned home a low cross at the far post to give the hosts the lead.
They almost had a second two minutes before the break, but the palm of Howard denied Bobby Reid from an acute angle.
On the stroke of half time meanwhile, Wanderers were down to ten men as Morais received his second yellow card of the evening for a late challenge, with the referee blowing his whistle mere seconds later.
With no changes for either side at the break, the game got back underway.
And City attempted to double their lead early on, with Mark Beevers’ heroics ensuring that the ball was hooked away from goal at the vital moment.
Howard was then called upon to keep out the hosts once again, with him palming away Paterson’s drive from eight yards.
With ten minutes of the second half gone, Bolton made their first change with Sammy Ameobi replacing Craig Noone as the Whites looked for an equaliser.
Madine won a free-kick in a promising position too soon after, but King's set-piece into the mixer was cleared away by the City defence.
The two combined with 25 minutes to go for Bolton's best chance of the game, with Madine's header from King's cross being cleared off the line by Aden Flint.
On the counter though, Howard had to be at his best once again to keep out Callum O'Dowda's curling shot from six yards out.
Bolton weren't for lying down either, with Madine's thunderous long-range effort having Fielding back-peddling and smothering the ball at the second attempt.
It was very much end-to-end at Ashton Gate, and the home side eventually made one of their attacks count as his horribly deflected effort trickled into the net with 13 minutes remaining.
A harsh and bitter blow for Wanderers, they set about trying to pull themselves back into the clash with substitute Adam Le Fondre's shot from 20 yards calmly gathered by Fielding.
Come full time however, there had been no further goals as the ten-man Whites found themselves on the wrong side of a two-nil scoreline.