Saints reserves crashed to a 3-1 defeat against ten-man Pompey at Fratton Park - despite taking a first minute lead.
Leon Best put top-of-the-table Saints in front when he sent goalkeeper Andrew Guatelli the wrong way after being upended with less than 60 seconds on the clock.
But that was as good as it got for Stewart Henderson's side, who missed a succession of first-half chances before suffering their second defeat in three games.
Pompey striker Vincent Pericard equalised within a minute of Best's spot kick. The Frenchman found the top corner from 12 yards but was withdrawn after a quarter of an hour following a clash of heads with Saints centre-back Allaedine Yahia.
Yahia received treatment for several minutes but looked as though he was still reeling when he deflected a Lomana Lua Lua cross against the woodwork.
He was replaced by Chris MacDonald shortly afterwards but the night belonged to Pericard's replacement, 18-year-old James Keene, who scored a decisive double after goalkeeper Guatelli was given his marching orders for hauling down Best in the 54th minute.
Best rounded Guatelli, only to be sent sprawling by the Pompey keeper, who was handed a straight red card by referee Richard Vaughan.
But Saints failed to create a chance of note against the home side's ten men while Keene twice beat Alan Blayney at the near post.
He gave Pompey a 2-1 lead within four minutes of the sending-off, cutting in from the left before firing home after good work from Richard Hughes.
And he added a second in injury- time, when he capitalised on a Chris Baird mistake before lifting the ball over MacDonald and beating Blayney on the half-volley.
It was not unlike Gazza's Euro '96 strike against Scotland but Saints could have had the game wrapped up long before then.
Martin Cranie had had to clear a Lua Lua shot off the line after a thrilling run from the former Newcastle striker but Best had earlier been denied by Guatelli's legs and Arron Davies provided two aerial chances for Dexter Blackstock, either side of a shot of his own that tested the Pompey keeper from 25 yards.
Blackstock forced Guatelli into an outstanding reflex save with a downward header and then sent a looping effort against the Italian's crossbar.
But Saints failed to register a shot on target in the last half hour.
Theo Walcott replaced Trinidad & Tobago midfielder Kenwyne Jones and played the last 20 minutes in his second appearance for the reserves.
But Walcott, Blackstock and Best were not given the service they needed.
Pompey coped comfortably and, as is often the case with a side reduced to ten men, hit the visitors on the break with clinical effect.
Comments: Our rules
We want our comments to be a lively and valuable part of our community - a place where readers can debate and engage with the most important local issues. The ability to comment on our stories is a privilege, not a right, however, and that privilege may be withdrawn if it is abused or misused.
Please report any comments that break our rules.
Read the rules hereComments are closed on this article