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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Live Text Commentary
Full Time The referee blows his whistle to end the game.90:00 +3:24
Inswinging corner taken right-footed by Ashley Harris from the right by-line.90:00 +2:57
Jed Wallace takes a shot. Curtis Nelson gets a block in.90:00 +0:42
Luke Young has an effort at goal from the edge of the area that misses to the right of the target.89:51
Free kick awarded for an unfair challenge on Conor Hourihane by George Colson. Jake Cole takes the direct free kick.86:56 Goal scored
Goal! - Nick Chadwick - Plymouth 3 - 0 Portsmouth Goal scored by Nick Chadwick from inside the box high into the middle of the goal. Plymouth 3-0 Portsmouth.85:03
The assist for the goal came from Maxime Blanchard.85:03 Goal scored
Goal! - Paris Cowan-Hall - Plymouth 2 - 0 Portsmouth Paris Cowan-Hall scores a headed goal from inside the six-yard box. Plymouth 2-0 Portsmouth.84:43
Inswinging corner taken by Paul Wotton from the left by-line,84:15
Inswinging corner taken from the left by-line by Paul Wotton, Dan Thompson makes a clearance.82:36 Booking
Booking Paris Cowan-Hall is given a yellow card.81:54
The assistant referee flags for offside against Paris Cowan-Hall. Simon Eastwood takes the free kick.81:00
Free kick awarded for an unfair challenge on Sam Magri by Paris Cowan-Hall. Simon Eastwood takes the direct free kick.78:30 Substitution
Substitution Paris Cowan-Hall joins the action as a substitute, replacing Matt Lecointe.78:17
Matt Lecointe is flagged offside by the assistant referee. Simon Eastwood restarts play with the free kick.77:37
Jack Maloney challenges Joe Lennox unfairly and gives away a free kick. The free kick is delivered right-footed by Paul Wotton from right channel, clearance made by Adam Webster.76:45
Adam Webster produces a right-footed shot from just outside the box that misses to the right of the target.75:09
Inswinging corner taken from the right by-line by George Colson, clearance made by Nick Chadwick.73:45 Substitution
Substitution Luke Young on for Johnny Gorman.71:32
Free kick taken by Paul Wotton.
Substitution Andy Higgins leaves the field to be replaced by Bradley Tarduck.71:32
George Colson gives away a free kick for an unfair challenge on Onismor Bhasera.69:07
Effort on goal by Dan Thompson from deep inside the penalty area misses to the right of the target.66:10
Curtis Nelson challenges Ashley Harris unfairly and gives away a free kick. Direct free kick taken by Jed Wallace.64:54
Ashley Harris produces a right-footed shot from just outside the box that goes wide left of the goal.64:15
Effort from the edge of the area by Nick Chadwick goes wide of the right-hand upright.59:01
Onismor Bhasera concedes a free kick for a foul on Dan Thompson. Andy Higgins crosses the ball from the free kick left-footed from right wing.56:14
Curtis Nelson concedes a free kick for a foul on Jack Maloney. Simon Eastwood takes the free kick.54:42
Matt Lecointe takes a shot. Save made by Jake Cole.53:56
Adam Webster takes a shot. Save made by Jake Cole.51:32
Outswinging corner taken by George Colson from the right by-line played to the near post, clearance made by Paul Wotton.50:13
Ashley Harris is ruled offside. Jake Cole restarts play with the free kick.49:03
Outswinging corner taken from the right by-line by Ashley Harris.48:45
Jack Maloney takes a shot. Blocked by Curtis Nelson.47:54
Free kick awarded for a foul by Curtis Nelson on Jed Wallace. Direct free kick taken by Dan Butler.45:01
The referee blows his whistle to start the second half.45:01 Substitution
Substitution (Plymouth) makes a substitution, with Joe Lennox coming on for Andres Gurrieri.45:00 +3:11 Half time
Half Time The match has reached half-time.45:00 +1:36
Johnny Gorman is caught offside. Adam Webster takes the direct free kick.44:46
Assist by Paul Wotton.44:46 Goal scored
Goal! - Johnny Gorman - Plymouth 1 - 0 Portsmouth Johnny Gorman finds the back of the net with a goal from inside the box to the top right corner of the goal. Plymouth 1-0 Portsmouth.43:24
Inswinging corner taken right-footed by Paul Wotton, clearance made by Alex Grant.42:39
Free kick awarded for an unfair challenge on Ashley Harris by Maxime Blanchard. Andy Higgins restarts play with the free kick, Ashley Harris produces a cross, save by Jake Cole.41:00
A cross is delivered by Johnny Gorman.40:25
Free kick awarded for a foul by Andres Gurrieri on Dan Butler. Alex Grant takes the direct free kick.34:37
Foul by Conor Hourihane on Jed Wallace, free kick awarded. Alex Grant takes the free kick.32:53
Paul Wotton produces a cross, Headed effort from deep inside the area by Maxime Blanchard misses to the left of the goal.32:53 Substitution
Substitution Jack Maloney replaces Ashley Westwood.32:53
Free kick awarded for an unfair challenge on Matt Lecointe by George Colson.26:39
Nick Chadwick takes a shot. Save by Simon Eastwood.26:01
Paul Wotton gives away a free kick for an unfair challenge on Andy Higgins. Andy Higgins takes the direct free kick.25:12
Nick Chadwick takes a shot. Simon Eastwood makes a save.20:26
Ashley Harris has a shot on goal from outside the area which misses left.20:08
The offside flag is raised against Nick Chadwick. Direct free kick taken by Simon Eastwood.18:31
Conor Hourihane concedes a free kick for a foul on Ashley Harris. Direct free kick taken by Alex Grant.15:29
Shot from just outside the area by Darren Purse goes over the bar.14:36
Alex Grant concedes a free kick for a foul on Nick Chadwick. Paul Wotton takes the direct free kick.12:48
Johnny Gorman takes the inswinging corner, clearance by Jed Wallace.12:23
Matt Lecointe takes a shot. Save by Simon Eastwood.10:48
Dan Thompson challenges Darren Purse unfairly and gives away a free kick. Jake Cole takes the direct free kick.9:14
Ashley Harris takes a outswinging corner to the near post.8:09
Andres Gurrieri has an effort at goal from just outside the box which goes wide of the right-hand upright.7:21
Dan Thompson is flagged offside by the assistant referee. Jake Cole takes the free kick.6:16
Unfair challenge on Matt Lecointe by Alex Grant results in a free kick. Onismor Bhasera takes the free kick.5:34
Effort on goal by Conor Hourihane from long distance goes over the crossbar.4:29
Effort from outside the penalty box by Curtis Nelson goes wide left of the target.4:09
Short corner taken by Johnny Gorman from the right by-line.3:46
Matt Lecointe takes a shot. Alex Grant gets a block in.1:58
Conor Hourihane has shot on goal from just outside the area which goes wide of the right-hand upright.1:41
Short corner taken by Paul Wotton.0:50
Foul by Dan Butler on Johnny Gorman, free kick awarded. Shot comes in from Johnny Gorman from the free kick, save by Simon Eastwood.0:10
Dan Butler challenges Nick Chadwick unfairly and gives away a free kick. Free kick taken by Johnny Gorman.0:00
The game kicks-off.
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