Read a match report of the Sky Bet League Two match between Southend United and Portsmouth at Roots Hall on Jan 1, 2014

Four years and two days ago, Portsmouth closed 2009 with a 4-1 defeat by Arsenal in the Premier League . Wednesday’s late loss at Southend left them four places and four points from going out of the league altogether.

It may have been undeserved because Portsmouth gave their new manager, Richie Barker, plenty of effort and enthusiasm and even took a first-half lead, but unless there is a huge improvement over the remainder of the season, a drop into the Conference Premier is a distinct possibility.

No player remains from the halcyon days of the Premier League under Harry Redknapp, and with it matches against the likes of AC Milan in European competition, but the fan base remains as committed as ever, as if the financial nightmare of the past four years had not existed.

In a crowd of 7,736, no fewer than 998 had travelled through the rain and gale-force winds from the south coast, and on other occasions they have been regularly taking up to 1,500 for matches at Bristol Rovers and AFC Wimbledon, grateful for their custom.

Barker has been in charge only for five matches since replacing the sacked Guy Whittingham but Portsmouth’s record of one win in 12 league and cup matches is relegation form by any standards and needs to be addressed if Pompey are to avoid the ignominy of a fourth relegation in as many years.

Barker said: “I am devastated with this latest result because the work rate was fantastic and this was one of our best performances since I took over. If there was a problem, it was that we did not deal with the long ball. But this is a necessarily young team and they will learn.”

Portsmouth’s loyal following had something to cheer in the first half as Southend, in sixth place at the start and now fourth, struggled to impose any kind of authority in difficult conditions. Having won at Fratton Park only five weeks ago after being reduced to 10 men, Southend might have expected an easier afternoon, but their goalkeeper, Dan Bentley, made important saves from Ricky Holmes and Jed Wallace to stop Portsmouth leading.

But in the 30th minute, Ashley Harris, on for head-injury victim Holmes, set up a goal for defender Sonny Bradley and it was no more than Portsmouth had warranted.

Phil Brown, the Southend manager, sent on proven scorer Barry Corr for Anthony Straker just before the break and Portsmouth were never quite the same force again. In the last minute of the first half, Ryan Leonard scored his first goal of the season from outside the area, with the aid of a deflection after Corr had created the opportunity.

Although Wallace hit the Southend bar there was an inevitability about the Southend winner in the last minute, an outstanding 25-yard shot from Leonard.

Brown applauded the way his team had fought back from being behind and pointed out that Southend were now only three points from top spot.

Meanwhile, the Portsmouth fans stayed behind at the final whistle to cheer their beaten squad, nothing dimming their enthusiasm in adversity, not even the memory of that Arsenal match four short years ago.

Match details

Southend (4-4-2): Bentley; White, Prosser, Phillips, Coker; Straker (Corr 40), Atkinson (Clifford 82), Timlin, Hurst; Leonard, Woodrow (Eastwood 68).
Subs Smith (g), Laird, Payne, Thompson.
Goals Leonard 45 90.

Portsmouth (4-5-1): Carson; Devera, N’Gala, Bradley, Painter; Holmes (Harris 20, Padovani 82), Whatmough, Racon, Connolly (Agyemang 69), Wallace; Bird.
Subs Ertl, Awford, Sullivan (g), Maloney.
Booked Connolly.
Goal Bradley 30.

Referee D Phillips (West Sussex).
Att 7,736