Dael Fry delivered Neil Warnock’s wish by scoring his first goal in a Boro shirt - but it proved scant consolation as Bristol City ended their barren run by winning at the Riverside.
The Robins arrived on the back of a run of seven straight defeats and were watched from the stands by former Boro skipper Nigel Pearson, who had been confirmed as City’s new boss on the eve of the game.
And it was Pearson who was able to reflect on an immediate victory after the visitors scored three first half goals during a killer spell in the game.
To add to Warnock’s frustrations, striker Ashley Fletcher also picked up an injury early in the contest and had to be withdrawn.
Boro had started on the front foot and carved out a great opening after Duncan Watmore found Neeskens Kebano to feed Marc Bola. Saturday’s goalscorer looked to pull it back for Ashley Fletcher instead of shooting on sight himself, and a City defender got a vital touch to clear the danger.
At the other end, Paddy McNair read the game to perfection when Nakhi Wells was played in by Famara Diedhiou and the Northern Ireland international was on hand to clear the ball off the line. Marcus Bettinelli also had to react well to save from Diedhiou after another counterattack from the visitors.
But Boro were hit by a double blow midway through the first half, and never recovered. Diedhiou opened the scoring for the visitors when he found space to head home an Adam Nagy cross, and Warnock was forced into replacing the injured Fletcher, who was clearly in some discomfort.
Former Boro man Tomas Kalas came to City’s rescue when McNair showed his attacking instinct and after beating Diedhiou he drilled a shot past Daniel Bentley, but not Kalas, who was on the line.
And City responded almost immediately by scoring their second of the night. Wells and Diedhiou combined with the latter tucking the ball beyond the reach of Bettinelli to double the visitors' advantage.
It was three moments later, straight from one end of the field to the other. Diedhiou headed on a Bentley kick, and Wells was able to profit by running clear on goal before picking his spot to score past the stranded Bettinelli.
Nathaniel Mendez-Laing came on at half-time as Boro looked to attack the mountainous task ahead, and Warnock’s men were firmly on the front foot, Watmore going close with a curling effort which went just over the top.
Bola had a shot saved after a McNair free-kick caused problems at the back for the visitors and Kebano had a shot blocked after intelligent play by Watmore. That proved to be the last taste of the action for the latter pairing with Britt Assombalonga and George Saville coming off the bench.
Bentley also clawed away a Marvin Johnson corner via his own bar before having a hand in Boro’s consolation goal, which saw Fry score his first for Boro when he knocked the ball home from close range.