Crisis-hit Portsmouth had to field a near-youth team as they lost in the League Cup first round to Plymouth.
Pompey, who had to release all senior players to avoid liquidation, fielded nine teenagers in their starting XI.
First-team coach Ashley Westwood, 35, then went off injured to leave their entire outfield side aged 18 or under.
Plymouth's Johnny Gorman scored from a tight angle, Paris Cowan-Hall headed a second goal from close range and Nick Chadwick pounced for a third late on.
Seven of Portsmouth's team had not played a senior match before and Pompey manager Michael Appleton could only name three substitutes, including 15-year-old Jack Whatmaugh.
Pompey's summer departures
- Greg Halford (Nottingham Forest)
- Erik Huseklepp (Brann)
- Dave Kitson (Free agent)
- David Norris (Leeds United)
- Kanu (Free agent)
- Luke Varney (Leeds United)
- Aaron Mokoena (Bidvest Wits)
- Hayden Mullins (Birmingham)
- Tal Ben Haim (Free agent)
- Liam Lawrence (Free agent)
Visiting goalkeeper Simon Eastwood, 23, who signed on a non-contract basis hours before the match, was called into early action, fumbling a Gorman free-kick over the crossbar.
Eastwood was more convincing when he produced a fine save to deny Matt Lecointe's acrobatic effort, before Portsmouth's Alex Grant had to clear a Curtis Nelson shot off the line.
But the Pilgrims took a deserved lead just before half-time when Gorman, on-loan from Wolves, blasted home a well-struck left-footed shot.
Pompey's youthful side battled hard but conceded two goals in the last four minutes.
Substitute Cowan-Hall, who began his career at Portsmouth, headed in following good work from Maxime Blanchard and Chadwick sealed the victory with a finish from inside the penalty area.
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