Middlesex slipped to the bottom of the NatWest Pro40 Division One table after going down by 19 runs in their clash with Nottinghamshire at Lord's.
Despite Eoin Morgan top-scoring with 39, they were unable to deal with a solid bowling display from the Outlaws with Graeme Swann picking up three wickets for 27 runs as the Crusaders' bid to avoid the drop into the second division suffered a setback.
Things started well enough for the hosts as they skittled their opponents out for 180, Tim Murtagh taking three for 42.
However, their chase fell short, despite Morgan's efforts.
Andrew Strauss fell for just 13 and Ed Joyce soon followed for 18.
Dangerman Dawid Malan also fell early, bowled for 16, attempting a reverse sweep in Swann's first over and with 51 runs still needed from 10 overs Tyron Henderson (16) was bowled by Samit Patel after a couple of mighty sixes.
The game was up then and Middlesex must now realistically win their remaining two games to stand a decent chance of staying up.
Lancashire climbed above Middlesex when their game at Durham was abandoned without a ball being bowled.
That result meant Durham's faint title chances were finally ended.
That was one of three games to fall by the wayside.
In Division Two, Essex's title hopes suffered a slight setback when their clash with Warwickshire was abandoned.
They will, however, win the division if they beat Kent next Saturday at Canterbury.
The clash between Leicestershire and Northamptonshire also saw no action, with both sides taking a point.
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