Pompey’s losing run was extended to seven games as they went down 3-2 at home to Leyton Orient tonight.
An awful first-half paved the way for the loss, which made it the Blues’ worst run of defeats in 37 years.
Caretaker boss Guy Whittingham’s side were better after the interval but too many mistakes and missed chances proved costly.
None came clearer than Izale McLeod’s first-half penalty miss - summing up an insipid 45 minutes from the home side.
Darel Russell had a volley blocked early on before Martin Rowland’s effort was deflected wide for the visitors.
But then came McLeod’s chance to end the barren run in front of goal from the spot after Brian Howard was pulled down by Ryan Allsop in the 27th minute.
The striker’s effort down the middle was pushed away by Ryan Allsop, however, as the goalless spell continued.
It got worse for Pompey five minutes later when Kevin Lisbie was freed by Dean Cox and tucked the ball past Mikkel Andersen.
Gabor Gyepes then limped off 10 minutes before the break and was replaced by Ricardo Rocha, who was given an ovation on his return.
Pompey were sent out early for the second-half by Whittingham and Andy Awford - no doubt after being read the riot act.
But Orient doubled their advantage after 51 minutes when Moses Odubajo bundled his way through and tucked the ball through Andersen’s legs.
McLeod at least ended Pompey’s barren run of 546 minutes without a goal after 56 minutes.
When Nathan Clarke pulled down Paul Benson, the former Barnet striker stepped up to smash home from the spot.
But Lisbie then buried the visitor’s own penalty after 62 minutes when he was judged to have been pulled down by Rocha.
Hopes of a grandstand finale were lifted with a fine finish from Scott Allan with 25 minutes left.
But, despite plenty of huffing and puffing, Pompey could not get the leveller needed to end their losing streak.