The previous time Manchester City left Teesside it was in May after losing 8-1 in what turned out to be Sven Goran Eriksson's last match in charge. Last night represented a marginal improvement therefore but it was another defeat and Mark Hughes is struggling to impose his will on a City side that has won one of its last five in the league.
Hughes's intent was to attack a Middlesbrough team that had lost 5-0 here to Chelsea 11 days earlier but while the personnel and the 4-3-3 formation were adventurous, City did not impress as a coherent unit. Robinho had his moments, as did Stephen Ireland and Shaun Wright-Phillips, but on those occasions when City bypassed a disciplined Middlesbrough back four, Ross Turnbull was more resolute in goal than at other times this season.
Boro were tentative initially – they had not won here since August – but gradually Gary O'Neil began to influence midfield and a fortunate penalty award in the 53rd minute set Boro on their way.
When David Wheater and City's back-pedalling teenage striker Daniel Sturridge became entangled fractionally outside the City area, Wheater fell forward and referee Lee Mason's view was that Sturridge both fouled Wheater and that the contact was inside the area. Afonso Alves stepped up and converted the penalty.
"It was a tight call," said Middlesbrough manager Gareth Southgate, "but it looks like David had one foot in the box. You get your reward for being positive."
Hughes thought otherwise. "The lad [Wheater] is not in complete control and it's a coming together of legs more than anything," Hughes said. "The linesman didn't flag but then the referee's performance tonight was average, if that."
Southgate felt particular pleasure in the "patience" of Boro's play. The home crowd can get on Boro quickly but Southgate said: "It was important that we played in a controlled manner. We had an emotional buffeting in the last game here."
Southgate also dismissed a touchline spat with Wright-Phillips, during which the winger appeared to gesture with two fingers at the Boro manager. "I've seen him in the tunnel, he wasn't very happy with what I said," Southgate said.
"We were both in the wrong but it's finished now." Hughes said he saw nothing.
City had had the better of a first half of meagre entertainment but after Alves's penalty, the promise of Ireland and Wright-Phillips withered and though Turnbull made smart saves from Wright-Phillips and Vincent Kompany in the second half, the visitors were disjointed in many aspects of their play.
Boro, meanwhile, were stable rather than effervescent. Tuncay Sanli was a willing target and O'Neil was a bundle of midfield energy.
Deep into four minutes of injury-time, with City pressed forward, Tuncay and O'Neil broke away and after the Turk had squandered his chance in front of Joe Hart, O'Neil made no mistake with the rebound. With that Middlesbrough moved to ninth place, one below City.
Goal: Alves pen (53) 1-0, O'Neil (90) 2-0.
Middlesbrough (4-4-2) Turnbull; Wheater, Riggott, Pogatetz, Taylor; Aliadière, Digard (Arca, 75), O'Neil, Downing (A Johnson, 83); Tuncay, Alves. Substitutes not used: Jones (gk), Emnes, J Johnson, Grounds, Walker.
Manchester City (4-3-3) Hart; Onuoha, Ben Haim, Dunne, Richards; Ireland, Kompany, Elano (Fernandes, 67); Wright-Phillips, Sturridge (Evans, 77), Robinho. Substitutes not used: Schmeichel (gk), Garrido, Berti, Hamann, Jo.
Referee: L Mason (Lancashire).
Booked: Middlesbrough O'Neil; Manchester City Kompany, Ireland, Robinho.
Man of the match: Turnbull.