Our look at Pompey's 2013/14 opponents continues with the Shrimpers
Meetings with Pompey
The first match between the sides was a Southern League clash in 1909 that ended in a goalless draw. Joseph Dix then scored as the return match at Fratton Park ended in a 1-1 stalemate.
Southend won 2-1 when the sides met in the Football League for the first time in 1920, although Pompey won 3-0 on their patch the following week.
The sides faced off eight times in Division Three (South) between 1920 and 1924, but then did not meet until 1961.
One of the most memorable matches occurred in May 1983 when goals from Kevin Dillon and Alan Biley clinched Pompey’s return to Division Two.
The most recent game at Fratton Park was in 1996, with Lee Russell scoring Pompey’s winner. Paul Hall then netted in a 2-1 defeat for the Blues at Roots Hall in March 1997.
The club were formed in 1906, competing in the Southern League until they became founder members of Division Three in 1920.
They remained in the third tier until suffering their first ever relegation in 1966, which was followed by a first ever promotion in 1972.
More ups and downs followed, but Southend were forced to sell many of their top players in the early 1980s because of financial problems.
The club narrowly avoided having to seek Football League re-election in 1985, while fans also discovered £70,000 of a Christmas savings scheme had gone missing and the club was in more than £800,000 of debt.
But the tide soon turned and Southend found themselves in the second tier for the first time in their history in 1991. They went on to finish 12th – their highest position to date.
Towards the end of the decade, however, they found themselves back in the basement thanks to successive relegations.
The Shrimpers were beaten by Blackpool and Wrexham in successive Football League Trophy finals in 2004 and 2005, but were promoted via the play-offs in the latter year and were then crowned League One champions in 2006.
The Shrimpers spent just a single season in the Championship before being relegated and lost out on the play-offs the following year.
They were hit by a winding-up order in 2009 because of a £690,000 unpaid tax bill and were relegated to the fourth tier in 2010.
Southend equalled a club record by going 17 games unbeaten in 2011 and finished 11th in League Two last term.
Information for Pompey fans
Away supporters can normally be found at the Blue Boor pub on the main Victoria Road near the ground.
The Spread Eagle is for home fans only, but Bar Victoria Court, The Bell (Toby Carvery) and The Railway Tavern are all nearby and more pubs can be found in the town centre.
Travelling by road
Postcode: SS2 6NQ
Distance from Fratton Park: 123.3 miles
Estimated drive time: 2 hours 25 minutes
Leave the M25 at Junction 29 and follow the A127 to Southend. Continue towards the town centre, through the lights near to the Bell Pub. At the next roundabout turn right (third turning), continuing on the A127. The ground is on the right just past the next traffic lights. If you turn right as you reach the ground, this will put you behind the away end where there is plenty of street parking to be found. Otherwise there is a car park behind the main stand which costs £5. The Southend High School For Boys also offers car parking for £5 per car (the school entrance is on Prittlewell Road).
Travelling by rail
The closest station to the ground is Prittlewell, which is a five minute walk away. Southend Central is a 25-minute walk from Roots Hall. The train journey from Portsmouth stations tales approximately three-and-a-half hours. Trains to Prittlewell from London Liverpool Street take 50 minutes. The standard adult fare not booked in advance is £43.90.
League Two fixtures
Pompey v Southend: Tuesday, November 26 (7.45pm)
Southend v Pompey: Wednesday, January 1 (3pm)