It has happened before as a bitter-sweet double, Cup final and relegation in the same season, and Middlesbrough are still battling on both fronts. Yesterday at Maine Road they remained on course for the Wembley half after a textbook away performance of contain and counter.
Having absorbed all that a spirited Manchester City side could throw at them, Georgi Kinkladze in particular, they broke out to grab a winner through their own exotic No 10, Juninho, to add an FA Cup quarter-final place to the Coca-Coca Cup semi-final they contest this week.
The unusual nature of this year's competition, stripped as it is of the biggest clubs, was embodied in this match, with City, in the First Division relegation zone, and Middlesbrough, bottom of the Premiership, vying for a place in the quarter-finals.
Despite the lowly positions, it was an intriguing prospect. After their turbulent season of changing managers and slipping ever downwards, City went into the match unbeaten in all seven matches since Frank Clark took over. Middlesbrough, meanwhile, have proved themselves an accomplished knockout team this season.
Above all, there was the promise of the dribbling contest between Kinkladze and Juninho, though initially space was at a premium with each side closing the other down swiftly in a fevered cup-tie atmosphere.
Boro began with the more composure, seeking to draw the sting from City and dousing the crowd's ardour by retaining possession. When City did succeed in working the ball to Kinkladze, he often found himself confronted by two or three Boro players ready to snap at his heels.
Still, City managed to fashion a couple of half-chances which suggested that they have become a more organised and disciplined outfit since Clark's arrival. A 25-yard shot from Steve Lomas drifted just wide and, after Nicky Summerbee had kept the ball in at the byline and found Uwe Rosler, Michael Brown almost reached the cross at the far post. Instead he connected with Neil Cox and was booked.
Middlesbrough responded with a low cross by Phil Stamp that just eluded Fabrizio Ravanelli and a shot by Juninho that was deflected wide. Otherwise, City were the more convincing attacking outfit and might have taken the lead when Ben Roberts dropped Rae Ingram's cross and the ball fell to Summerbee. However, his side-foot was weak and wide.
The game was in a messy, attritional phase with Robbie Mustoe and Stamp for Boro and Lomas for City all booked in the space of two minutes. We awaited a little inspiration to lift it.
We almost got it just before half-time when Lomas cut in from the left, crossed for Kit Symons on the edge of the box, he headed the ball forward, and Ian Brightwell turned the ball home. Offside, decreed a linesman, though a television replay suggested otherwise.
City brought the encouragement of having pierced the visiting defence with them into the second half, however. Kinkladze threaded a delightful ball into the penalty area for Summerbee, only for him to send his shot over the bar. Then another neat run by Kinkladze opened up Boro again, Curtis Fleming intervening at the last to clear.
Finally, stung perhaps, Boro emerged from their shell to create a clear- cut chance. Juninho played a neat pass out to Stamp on the right and his cross found Ravanelli in space, but the Italian glanced his header wide.
Soon after, Symons headed Kinkladze's free-kick over the bar as Boro were forced back again, but when the Georgian went off the field with an ankle injury, one sensed that City's best chance of winning had gone with him.
The substitute Paul Dickov claimed, unsuccessfully, a penalty when Cox tackled him from behind, but a now more comfortable Boro seemed to sense that the worst was over and duly they broke out to pinch a goal. Gianluca Festa and Ravanelli worked the ball to Juninho at the far post and the little Brazilian promptly drilled the ball home.