Pools Reserves suffered a miserable day at the Don Valley Stadium as they went down 3-2 to Rotherham United in the Totesport.com League.
Denis Behan was stretchered off early in the game with an ankle injury, while Michael Mackay missed a penalty during an afternoon when nothing seemed to go right for Colin West's men.
The Millers took the lead on twenty minutes when Micky Cummins sent an incisive through ball to Ryan Taylor who fired home at the second attempt after Mark Cook had saved his initial shot.
Cook had to be at his best moments later to prevent the hosts doubling their lead when Marcus Marshall fired on goal after more good work from Taylor.
Jon-Andre Fredriksen almost equalised when he slung a free-kick in on goal but found keeper Jamie Annerson in top form and he tipped it round the post.
However, the leveller arrived right on half time when Behan's replacement Billy Greulich turned neatly to drill home off the underside of the bar after a scramble in the area.
Earlier after the restart Armann Bjornsson was felled in the box and the referee pointed to the spot only for Michael Mackay to see his penalty saved.
Pools were made to pay for the miss when Rotherham went in back in front minutes later, this time it was trialist Taiwo Atieno who found the net after a great cross from Gary Roberts.
A minute later it was 3-1 and the game was drifting away from Pools when Taylor scored his second of the afternoon with a sweet left-foot strike.
With twenty minutes left, Greulich gave Pools hope of snatching something when he took advantage of a defensive slip to slide the ball past Annerson and make it 3-2.
But Pools couldn't find another way through and were left to ponder defeat for the first time since the turn of the year.
Full Time: Rotherham United 3 Pools 2
Pools: Cook, McSweeney, Clark, Cherel (Marron 61), Haslam, Mackay, Rowell, Power, Fredriksen (Martin 63), Behan (Greulich 17), Bjornsson.
Subs not used: Herbert, C Liddle.