The biggest winnings in betting on Chesterfield matches

Chesterfield, an English football club from the county of Derbyshire, which plays in the National League, has repeatedly become the hero of incredible success stories in bookmaker betting. Despite the fact that the club is not one of the greats of English football, its matches sometimes brought players fantastic winnings due to sensational results.

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The English Cup sensation: Chesterfield vs Middlesbrough (1997)

One of the most high-profile stories associated with Chesterfield was their incredible run in the 1996/97 English Cup. The club, which was then in the third-highest division of English football (the Second League), reached the semi-finals of the tournament, which was a sensation in itself. The match against Middlesbrough, a team from the Premier League, which took place on April 13, 1997, at Old Trafford, attracted special attention.

Chesterfield was considered a clear underdog, with odds of 12.00 on their victory. The match ended in a 3-3 draw after normal time, which came as a shock to the football world. Chesterfield led 2-0 with goals from Sean Ditch and Kevin Davis, but Middlesbrough managed to equalize the score. In extra time, the teams exchanged goals, and the match went to a replay. One fan who bet £50 on a draw won £600, as the odds for this outcome were around 12.00. In the replay, Middlesbrough won 3-0, but the draw in the first match remains one of the greatest Cup of England surprises.

This match attracted the attention of many players who believed in Chesterfield as a team capable of surprising others. Some of them, having placed bets on an exact score of 3:3, won the jackpot with odds higher than 50.00.

Winning the League Cup against Manchester City (2006)

Chesterfield, who were playing in Ligue 1, faced a Premier League club that then included stars such as Joey Barton and Bernardo Corradi. The odds for Chesterfield's victory reached 8.00, making them clear underdogs.

The match at Saltergate Stadium ended in a 2:1 victory for Chesterfield. Caleb Folan scored the first goal in the 36th minute, and Colin Larkin sealed the victory in the 66th minute. Manchester City responded with only one goal from Georgios Samaras in the final minutes. One of the fans who placed a £200 bet on Chesterfield's victory received a significant win of £1,600, which was a substantial amount at the time. Other players who risked betting on an exact score of 2:1 earned even more: the odds for this outcome exceeded 20.00. For example, there was a case where a bet of £50 earned £1100.

An unexpected draw with Portsmouth (2014)

In the 2014/15 season, Chesterfield once again surprised the football world by drawing with Portsmouth in a League 1 match that took place on November 3, 2014. Despite their financial difficulties, Portsmouth were considered the favourites due to their historical status and squad. The odds for a Chesterfield win were around 3.50, while the odds for a draw were 3.80.

The match ended in a 0-0 draw, which was a disappointment for Portsmouth but a joy for Chesterfield fans. One player who placed a £300 bet on a draw won £1,140, making it one of the biggest winnings from the match. Other fans who risked on an exact score of 0:0 earned even more, as the odds on this outcome reached 10.00. For example, a bet of £100 earned one of the players £1000.

The historic match against Tranmere Rovers (2014)

Chesterfield achieved a convincing victory with a score of 3:1, which was a surprise considering the equal level of the teams. The odds on a win were around 2.50, and the odds on a 3-1 score were around 15.00.

Oli Banks, Gary Roberts, and Mark Richards scored goals for Chesterfield, allowing the team to dominate the field. A fan who bet £500 on their team's victory received £1,250. Another player who bet £100 on a 3-1 score earned £1,500.

League 2 Play-Off Victory (2001)

The League 2 play-off match against Barnet on 13 May 2001 was another chapter in Chesterfield's history. The club won 3-0 to secure promotion to a higher league. The odds on Chesterfield's victory were around 2.00 but some players took a chance on a big score. David Reeves, Mark Ollott, and Luke Beckett scored goals, making the match a celebration for fans.

One player who placed a £1,000 bet on Chesterfield's victory received a £2,000 payout. Another player who placed a £100 bet on a 3-0 victory with a 12.00 odds turned their £100 bet into a £1,200 win. This game showcased Chesterfield's ability to not only entertain fans but also provide significant rewards to those who believe in their success.