Date: 26th October 2020 at 8:12pm
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Over the course of the Premier League years, we have seen multiple transfers not work out as clubs expected. But which signings are the most regretted of all time? Here is our selection of the top five.

Mario Balotelli’s Transfer to Liverpool

Replacing Suarez was always going to be a challenge. But Liverpool could have made a much better decision than selecting Mario Balotelli. However, there was some logic behind the Reds’ decision. Balotelli was only 24 years of age in 2014, and he had just completed a 14-goal season for Milan. It was not long before Liverpool realised it had made a mistake in paying out £18 million for Balotelli’s transfer, though. He only scored one goal during his time with the Reds, and his poor performance contributed to manager Brendan Rodgers being sacked. Even fans who love betting on players and games could not have predicted such a catastrophe for both Balotelli and Liverpool. On a related note, if you’re looking to gamble on the forthcoming season, you may want to check out the betting on Casumo for the latest football odds.

Bosko Balaban’s Transfer to Aston Villa

After Aston Villa signed Bosko Balaban from Croatian club Dinamo Zagreb in 2001, it took him eight months to complete a full match, and even that was in the reserves. Balaban simply never got started. Over eight appearances, the striker never struck. After playing for only a total of 138 goalless minutes, he was loaned back to Dinamo. But Balaban threatened to spend the 30 remaining months of his contract in the reserves, so Villa eventually had to settle a deal. If Balaban’s transfer had not cost £7 million, Villa would not have regretted his transfer as much as they did. £7 million may not sound a huge amount by today’s standards, but back in 2001, Balaban’s signing with Villa was the 23rd largest transfer of the year by a Premier League club.

Danny Drinkwater’s Signing to Chelsea

Seeing as Danny Drinkwater had been integral to Leicester’s title win of the previous year, it seemed to make sense at the time for Chelsea to sign the midfielder. The club snapped him up for £34.1 million in 2017. However, things did not pan out as hoped. Drinkwater made 12 appearances in his debut Chelsea Premier League season, but his performance was far from strong. And when new manager Maurizio Sarri took over, Drinkwater made no league appearances at all during the 2018 – 2019 season. With Drinkwater reportedly on a salary of £100,000 per week with the Blues, he has become one of the worst signings the club ever made.

Ricky Alvarez’s Transfer to Sunderland

Argentine Ricky Alvarez began his professional career with Vélez Sársfield in 2008. His top-notch appearances enabled him to move to Inter Milan in 2011. During the 2014-15 season, the attacking midfielder joined Sunderland on loan. The agreement in place stated if Sunderland secured its place in the Premier League for the following season, Alvarez would automatically become a permanent signing, for around £9.5 million. Sunderland did indeed manage to stay in the Premier League, but Alvarez only played 13 games because he suffered a knee injury. Because the injury had undergone microfracture surgery years before, Sunderland tried to get out of its transfer agreement. The Black Cats did not succeed. Neither did they offer Alvarez a contract. That meant Sunderland paid out over £9 million for a player who immediately left the club! To add insult to injury, that allowed Sampdoria to sign Alvarez on a free transfer.

Ali Dia’s Transfer to Southampton

Southampton manager Graeme Souness must have regretted this transfer early on. The Ali Dia transfer of 1996 is unquestionably one of the most bizarre signings in Premier League history. The story goes that a man pretending to be notable player George Weah telephoned Souness. The man recommended that Souness signed his cousin Ali Dia, after informing the Saints manager that Dia had scored two goals for Senegal the week before and had previously played for Paris Saint-Germain. The truth is Dia was actually a 31-year-old student who only occasionally played non-league footie. Souness brought Dia in on trial and during his only match, against Leeds, the newcomer was substituted for Matt Le Tissier in the 32nd minute of the game. After 53 minutes of play, it was clear Souness had made a mistake, and Dia came off the pitch, never to return to league football.

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