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Nightmare debut was sign of things to come for Frimpong at Barnsley. Tykes gambled on him after Arsenal exit but didn’t pay off

In January 2014, with Barnsley in the Championship relegation zone, manager Danny Wilson signed Emmanuel Frimpong on a six-month contract from Arsenal, a deal which appeared bizarre from the outset and would go down as one of the worst transfers in the history of the football club.

As 2014 began, the Tykes were deep in relegation trouble in the Championship. Wilson was in his second managerial term at Oakwell, having taken over from David Flitcroft, who had been sacked due to the club's poor form.

One of the most bizarre transfers ever at Oakwell

The January transfer window was an opportunity for Barnsley to bring in players who could spark their season into life and hopefully help the club retain its Championship status. In one of the club's most bizarre signings, the Reds faithful watched as Frimpong was signed from Premier League side Arsenal on a six-month contract for an undisclosed fee.

The signing raised eyebrows, as the Yorkshire club were prepared to sign a player who had not played a game of football that season. In the previous campaign, Frimpong only played 14 times, so he was well short of match sharpness when he walked through the doors of Oakwell.

Starting his career at Arsenal aged nine years old, Frimpong was successful in the Gunners' youth side, helping them win a League and FA Youth Cup double in 2009 and retain their league title again the next year.

After making it to the first team under Arsène Wenger, playing in the Premier and Champions League, Frimpong found himself surplus to requirements and was loaned out to firstly Wolves, then Charlton and Fulham before his permanent move to Barnsley.

There was clearly pedigree there but the Tykes' Arsenal gamble would soon go wrong.

Frimpong was thrown straight into the Barnsley squad and a small matter of a South Yorkshire derby away at Sheffield Wednesday. Maybe the Ghanaian tried a little too hard to show he was up for the battle against the Reds' fiercest rivals.

After 30 minutes, referee Andre Mariner gave Frimpong his second yellow card and his marching orders after committing two fouls on the same player, Chris Maguire, in a short space of time.

Getting sent off so early on your debut isn't something that endears you to the manager, teammates, or supporters. Two other players followed Frimpong down the tunnel after seeing red, Wednesday's Jermaine Johnson and Barnsley's Jacob Mellis. The Owls won the game 1-0 courtesy of a 97th-minute goal by Maguire, who was on the receiving end of treatment from the debutant Frimpong.

It was a nightmare start but a sign of things to come.

The midfielder's time at Oakwell was all too brief, managing only nine appearances and racking up five yellow and one red card in that time.

By the end of the season, Frimpong moved on to sign for Russian side FC UFA and Barnsley were relegated to League One alongside Yeovil Town and Doncaster Rovers after finishing the season in 23rd place, only amassing 39 points from 46 games.

A sour end to a miserable season for Barnsley and the end of a brief but explosive transfer that will forever be remembered for all the wrong reasons.