Football in England is full of surprises, especially when it comes to matches involving modest clubs like Eastleigh Town. This National League club has shocked fans and analysts on more than one occasion, bringing huge winnings to those who dared to bet on the underdog.
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Match against Portsmouth in the FA Cup (2007/08)
In the 2007/2008 season, Eastleigh Town, then playing in the Southern Conference (sixth tier), entered the third round of the FA Cup against Portsmouth, the Premier League champions and previous year’s cup winners. Portsmouth were considered the clear favourites: the team, with stars such as Sol Campbell and David James, had odds of around 1.10 to win, while Eastleigh had odds of 15.00 and above.
The match took place on 5 January 2008 at Silverlake Stadium in Eastleigh. The weather was freezing and the pitch was heavy, which played into the hands of the hosts. Eastleigh started aggressively: in the 11th minute, forward David Farrell opened the scoring after a counterattack. Portsmouth responded before half-time, but in the second half, Eastleigh scored twice more, with goals from Peter Gillespie and Andrew Bowle. The final score of 3-2 in Eastleigh’s favour was a sensation.
This victory brought huge winnings: a single bet on Eastleigh to win outright at odds of 17.00 returned £170,000 from a stake of £10,000.
The game against Bolton Wanderers in the League Cup (2015/16)
In August 2015, Eastleigh Town was drawn against Bolton in the first round of the League Cup (EFL Cup). Bolton, representing the Championship (second division), was the clear favourite with odds of 1.40 to win. Eastleigh, from the National League, were priced at 6.50–8.00, given the difference in class.
The match took place on 11 August at Eastleigh’s University Stadium. Bolton took a 1-0 lead in the 25th minute thanks to a goal from Zaccoli, but Eastleigh equalised in the 38th minute with a goal from Chris Fulton after a corner. In the second half, Richard Killie’s team surprised everyone: in the 62nd minute, James Stirling scored from a free kick, and in the 78th minute, Paul Jackson sealed the victory. The score was 3–2, and the sensation was complete.
The winnings were huge. A bet on Eastleigh to win at odds of 7.50 earned one player £75,000 from a £10,000 stake. An even bigger jackpot — £150,000 — went to someone who bet £20,000 on Eastleigh with a +1.5 handicap at odds of 7.50.
Victory over Winchester City in the derby (2018/19)
In January 2019, Eastleigh Town faced their neighbours Winchester City in the National League in what is considered the Hampshire derby. Winchester were leading the Southern Group table, while Eastleigh were fighting for survival. The odds reflected this: 2.20 for Winchester, 3.20 for a draw and 3.50 for Eastleigh.
The game on 12 January at Club Meadow Stadium was played in a tense atmosphere with 2,000 spectators. Winchester scored first in the 15th minute (goal by Cormac Tyler), but Eastleigh responded in the 32nd minute with Michael Cosgrove finishing off a cross. In the second half, Chris Fulton put the hosts ahead with a header in the 55th minute, and Paul Jackson scored the fourth in the 72nd minute after a defensive error. The final score was 4-1, a crushing defeat for the favourites.
Bets on Eastleigh at odds of 3.80 brought a £380,000 win to one player who bet £100,000 (a rare big win). Another case — £200,000 from a £50,000 bet on “Eastleigh to score more than 1.5 goals” at odds of 4.00.
Away triumph against Sutton United (2020/21)
In the 2020/2021 season, during the pandemic, Eastleigh visited Sutton United in the National League on 6 March 2021. Sutton was in the play-off zone, Eastleigh was in the middle of the table. Odds: 2.10 for Sutton, 3.60 for Eastleigh.
The match at Grub Road Stadium began with a goal from the hosts in the 10th minute (Ishmael Dudsons). Eastleigh equalised in the 28th minute with a goal from Roan Birch from outside the penalty area. In the second half, Michael Cosgrove scored the second goal in the 52nd minute, and Chris Fulton made it 3-1 in the 67th minute. Sutton reduced the deficit to 3-2, but Eastleigh held on for the win.
This game yielded big winnings: a bet on Eastleigh +0.5 with odds of 1.90 brought in 190,000 from 100,000, but the bigger jackpot was 500,000 with odds of 5.00 on a straight win.