The football club from Southend-on-Sea, which plays in the National League, England's fifth-tier division, is not one of the giants like Manchester United or Liverpool. Nevertheless, this team's matches have been the basis for some impressive betting wins thanks to unexpected results and high excitement.
League 2 Play-offs (2004/2005): Victory over Lincoln City
One of the most memorable moments in Southend United's history, according to beonbet-uk.com/, was the 2004/2005 season, when the team fought for promotion to League 1 through the League 2 play-offs. The climax was the final match against Lincoln City on 28 May 2005 at the Millennium Stadium in Cardiff. Southend was considered the underdog, as Lincoln City had shown consistent results throughout the season. The odds for Southend to win in regular time were 3.50–4.00, which attracted the attention of risk-taking players.
The match ended 2–0 in favour of Southend United in extra time. Freddie Eastwood scored the first goal in the 105th minute, and Duncan Japp scored the second in the 110th minute. This victory was a sensation, as Southend not only overcame the resistance of a stronger opponent, but did so in a tense battle. One fan from Essex reportedly bet £50 on Southend to win the play-off at odds of around 4.00. His winnings amounted to £200, which was a significant sum for local fans at the time.
Essex derby: Victory over Colchester United (2006)
The Essex derby between Southend United and Colchester United is one of the most heated rivalries in the lower divisions of English football. In the 2006/2007 season, when Southend played in the Championship after triumphing in League One, the match against Colchester on 25 November 2006 was a real event. Southend were considered underdogs due to their inconsistent results at the start of the season, and the odds on them winning away were as high as 5.00.
The game ended 3-0 in Southend's favour. Club legend Freddie Eastwood scored twice (in the 31st and 76th minutes), and Mark Gower added a third goal in the 83rd minute. This result came as a shock to Colchester fans, who considered their team to be the favourites. One local resident reportedly placed a £100 bet on Southend to win at odds of 5.00, which earned him £500.
FA Cup (2024): Draw with Cambridge United
In the 2024/2025 season, Southend United participated in the FA Cup, where they faced Cambridge United in the first round on 2 November 2024. This match was another example of Southend's unpredictability. The game ended in a dramatic 3-3 draw in extra time. Jack Bridge (45 1'), Ben Cocker (52') and Rhys Edwards (90 3') scored for Southend, while Cambridge responded with goals from Liberna (9'), Mitchell (40'), Godden (66') and Ahadme (120 1'). The odds for a draw in this match reached 3.80, as Cambridge were considered favourites due to their more consistent form.
According to reports, one fan from Southend-on-Sea bet £200 on a draw, relying on Southend's historical tenacity in cup matches. His winnings amounted to £760, which became one of the most talked-about stories in local pubs after the game.
League 2 Play-offs (2015): Success against Stevenage
Another significant match took place in the League 2 play-offs of the 2014/2015 season, when Southend United faced Stevenage. The two-legged tie ended with a 4-2 aggregate score in Southend's favour. The first game ended in a 1-1 draw, and in the second, Southend was behind but managed to equalise in regular time and score two goals in extra time (both by Freddie Eastwood). The odds for advancing to the next round were around 3.20, which attracted the attention of players looking for high odds.
One fan reportedly bet £300 on Southend to reach the playoff final, which earned him around £960. This case is an example of how belief in a team and analysis of its form can lead to significant winnings, especially in the playoffs, where underdogs often work miracles.