Whether you're a fresh faced teenager or seasoned professional with 20-years at the top under your belt, making your first appearance in the League Cup is always a daunting prospect. The competition has seen some corkers during its 52-year life span and also some unforgettable ordeals that some poor souls failed to recover from. There is no escaping the ignominy of a nightmare début and whether you go on to become a world beating, trophy hogger everyone will still remember that frosty night in Middlesbrough when you scored that own goal. So without further ado, meet the players who'd rather you forget their first forays into the League Cup.

Jose Antonio Reyes – Arsenal

Arsenal fans still recoil in horror over the subject of Reyes’ full debut for the club and first experience of the League Cup in the 2004 semi-final against eventual winners Middlesbrough. The £10.5 million signing from Sevilla was never noted for his defensive capabilities and it showed in spectacular fashion as he scored an own goal five minutes from time to send Boro through to the final.

Wayne Bridge – West Ham United

Signed on loan to add some experience to West Ham’s fight against relegation in 2010/11, Bridge’s first appearance in the League Cup for his new club couldn’t have gone any worse. The former England defender endured a torrid evening in the second leg of the semi final against Birmingham as the Hammers relinquished their 2-1 aggregate lead, losing 3-1 on the night and 4-3 overall.

Jonny Evans – Manchester United

Taking to the field for the first time in a Manchester United shirt is a momentous occasion for any player. However, it’s probable that Jonny Evans will want to forget his Red Devils debut. The then 19-year-old lined up in a defence that was breached twice and dumped out of the cup by Championship side Coventry.

Ashley Cole – Arsenal

Despite being recognised as England’s greatest left back and possessing a trophy cabinet bursting at the seams with silverware, Cole’s debut for Arsenal in November 1999 was one to forget. He was just 18 years of age at the time he came on for Ray Parlour in the second half but couldn’t prevent the Gunners from losing on penalties.

Brad Jones – Liverpool

When Jones lined up against League Two side Northampton on his Liverpool debut two years ago, victory was supposed to be routine. Unfortunately for the keeper he played his part in one the greatest nights in the Cobblers’ history as they left Anfield victorious after a penalty shootout.

Marco Ambrosio – Chelsea

Joining Chelsea at the age of 30, many eyebrows were suitably raised by Claudio Ranieri’s decision to sign Ambrosio from Chievo in June 2003. His awful debut in a League Cup tie with Notts County did nothing to persuade supporters that he would be a useful acquisition making a dreadful blunder when coming out to collect a loose ball and presented the old Division Two side with a goal.

Phillip Degen – Liverpool

Despite being seen as one of the major flops of Rafael Benitez’s final season in charge at Anfield, it seems harsh to criticise Degen given what happened to him on his debut. A League Cup tie against lowly Crewe Alexandra seemed the perfect opportunity to introduce the Switzerland fullback to English football. Sadly he broke two ribs and punctured a lung following a collision with Sami Hyypia and never really got going at Anfield after that.

Phil Neville – Manchester United

As unforgettable debuts go Neville’s must rank right at the very top playing his part in one of the greatest giant killings in League Cup history as Division Three stalwarts York walloped Manchester United 3-0 at Old Trafford. To compound his misery Neville was asked to play in an unorthodox right wing position and gave the ball away for the first goal. The rest of his career didn’t turn out too badly mind you.

Pat McGibbon – Manchester United

Just like teammate Phil Neville, the humiliating defeat to York also marked McGibbon’s debut for Manchester United. Sadly it proved to be his first and only appearance for the Red Devils as he was shown a red card for hauling down Paul Barnes in the penalty area with the striker duly converting from 12-yards to put his team 2-0 up.

Curtis Davies – Aston Villa

Davies’ confession that his performance on his Aston Villa debut was akin to that of a ‘pub team player’ was refreshing if not a little saddening. Sadly for the Villans they crashed out of the League Cup that night going down 1-0 to Leicester.