The son of Teddy Sheringham inspired Pompey’s downfall as Andy Awford’s men suffered a 3-0 defeat this afternoon.
The Blues headed to Ebbsfleet free-scoring and in-form having impressed in their previous three friendlies.
Yet they ended up comfortably seen off by a Fleets side which have now picked up a trio of Football League scalps this summer.
Charlie Sheringham - son of Teddy - grabbed two and Billy Bricknell the other for the eye-catching hosts.
At the other end, Pompey failed to test the keeper enough and in the first-half in particular shot wide from highly promising positions.
They now face Bournemouth on Tuesday as they head towards the August 9 league start.
Ebbsfleet first tested Paul Jones in only the third minute when Bricknell twisted and turned before drilling in a shot held low down by the keeper.
Jed Wallace would engineer the Blues’ first attempt, beating the off-side trap to line-up a shot which fizzed past the far post.
Moments later the midfielder produced a similar effort with a similar outcome having been fed down the left.
The deadlock was broken in the 20th minute when Bricknell got free down the right and whipped in a cross turned in at the near post by Sheringham.
Just five minutes later Bricknell cleverly wrong-footed Chorley and drilled in a shot beaten out at the near post by Jones.
In their search for an equaliser, Adam Webster shot narrowly past the post and then Danny Hollands’ mis-hit left-foot volley went comfortably wide.
The Fleet remained in the lead at the break and Pompey made their first substitution with Miles Storey introduced for Ryan Taylor.
Yet the hosts increased their lead in the 54th minute when Joe Howe delivered a cross from the left and the unmarked Bricknell glanced a header home.
It would get even worse four minutes later when Anthony Cook was too strong for Webster down the flank and when his cross was parried by Jones, Sheringham followed it up to make it 3-0.
The 62nd minute would signal six substitutions but it would do little to turn the game back in the Blues’ favour.
Patrick Agyemang did feed Alex Wynter 10 minutes from the end but he could only stab it straight at the keeper, while Preston Edwards pulled off a decent save from Storey.
But it ended up in a 3-0 loss for Awford’s men on their visit to Stonebridge Road.