By no means is the promotion dream over, but that day is edging closer and closer with Monday's trip to Plymouth a likely place for it to die.
Boro needed to defeat Crystal Palace at the Riverside Stadium and after quarter of an hour that looked on the cards.
Scott McDonald, unlikely to play at Plymouth after being risked after hamstring trouble today, slid in to convert Gary O'Neil's cross, despite claims for offside, and Gordon Strachan's men were up and running.
The problem, however, was that Strachan could only look on in frustration as his players failed to turn possession into goals for the rest of the encounter, leaving the door open for Palace to grab an equaliser.
That arrived on the stroke of half-time. Alan Lee's centre from the left was perfect and Alassane N'Diaye rose to nod the precise header inside Brad Jones' left hand post.
It might have kept Palace's hopes of staying in the Championship alive, but it also ensured that Middlesbrough look destined to be still in that division again next season too.
Middlesbrough had looked set to give their play-off hopes a real lifeline when McDonald put them ahead even if it led to massive complaints from the Palace defence.
The Aussie was in an offside position when Justin Hoyte fed Gary O'Neil through with a perfect pass down the right. And by the time O'Neil had worked his way into the box, McDonald slid in to finish the cross to open the scoring.
But with little for Palace goalkeeper Juilan Speroni to do in terms of saves in the first half, Middlesbrough had to make sure they kept the door firmly shut at the back.
But the equaliser arrived and stemmed from Lee's perfect centre from the left flank where Kyle Naughton had been introduced for Andrew Taylor minutes before and N'Diaye placed his neatly.
After the restart it was all Middlesbrough but, with the exception of a Barry Robson drive from distance that was turned around the post by Speroni, there was very little actually created.
And in the dying stages Speroni made an exceptional low save to his right to thwart a McDonald strike that had looked destined for the net. Instead Palace survived and Boro were left frustrated.
MIDDLESBROUGH (4-4-2): Jones; Hoyte, Wheater, McManus, Taylor (Naughton 42); Robson, O'Neil, Williams (O'Shea 78), Franks (Lita 58); Killen, McDonald. Subs: Coyne (gk), Miller, Arca, Grounds.
CRYSTAL PALACE (4-4-1-1): Speroni; Ertl, McCarthy, Davis, Lawrence; Ambrose, Derry, Danns, Carle (Scannell 72); N'Diaye; Lee (Andrew 78). Subs: Manns, John, Comley, Zaha, Holland.