Izale McLeod struck the only goal deep into extra time as League One Crawley dumped Ipswich out of the Capital One Cup with a 1-0 first-round victory.
It was the ninth time in the last 12 years that Ipswich have been knocked out of the competition by a team from a lower division.
Crawley striker McLeod shot narrowly wide early on before Town forward Frank Nouble blazed wastefully over from a good position after a long ball from Luke Chambers.
Former Chelsea and West Ham man Nouble was off target again midway through the half when he put the ball wide from a fine cross from Anthony Wordsworth.
McLeod had a shot blocked for the Red Devils before Town midfielder Paul Taylor was similarly denied at the other end shortly before the break.
The first shot on target arrived two minutes after the interval when Nouble forced Brian Jensen to make a low save to his left.
Debutant midfielder Kevin Bru later set up Taylor and he was just off target with a curling effort from 20 yards, and Taylor went close again when his goal-bound shot was parried by Jensen.
Ipswich got on top after the interval and substitute Balint Bajner forced Jensen to push his fierce shot round the post.
Town substitute Teddy Bishop almost snatched victory a minute from the end of normal time when his rasping 30-yarder came back off the underside of the crossbar.
But McLeod struck to put Crawley through after 111 minutes from close range after Town failed to clear a corner.