Nine debuts even worse than Moises Caicedo’s Chelsea nightmare - including West Ham and Southampton shambles

The thing with supposedly being worth £115 million is that a fee of such elephantine heft tends to bring with it a certain amount of heightened scrutiny. That being said, even if Moises Caicedo had cost Chelsea 115p, his debut on Sunday afternoon probably still would have been met with a considerable amount of criticism.

Introduced in the 67th minute of the Blues’ doomed visit to West Ham, the 21-year-old did little to positively impact the contest, and ultimately sealed his side’s fate when he conceded a penalty that Lucas Paqueta converted to hand the Hammers a 3-1 victory.

Indeed, so bad was Caicedo’s cameo that Jamie Carragher labelled his display ‘a bit of a nightmare’. But if nothing else, the Ecuadorian can take some solace from the fact that he is not the first professional footballer to ever have a serious off day in their first appearance for a new club. Check out some of the worst below...

Jonathan Woodgate

The absolute gold standard of debut shockers, Jonathan Woodgate signed for Real Madrid in August 2004, but was beset by injury complaints and had to wait a full 13 months to make his bow for the Spanish giants. By the time he was done, he probably wished that he was back in the safety of the treatment room.

The former Newcastle United defender firstly managed to score a quite spectacular diving header own goal, and then saw red in the 66th minutes after being punished for two bookable offences. Perhaps it is unsurprising that Marca readers voted him as the worst La Liga acquisition of the 21st century.

Emmanuel Frimpong

Fair warning, you’re going to be reading about a fair few sending offs on this list, but you might struggle to find a player who was dismissed for two different clubs on two separate debuts. Emmanuel Frimpong - cousin of Lethal Bizzle, for those who care about such things - did nothing but complain after signing for Barnsley in 2014, and his displeasure evidently spilled out onto the pitch when he saw red within half an hour of his first outing.

Interestingly, Frimpong was also sent off on his Premier League debut for Arsenal after picking up two yellow cards. Dench.

Tomas Repka

Tomas Repka arrived at West Ham with a reputation for aggression, and he lived up to it almost immediately by getting sent off against Middlesbrough in his very first appearance. By no means was that the end of the Czech’s disciplinary issues, however.

In his third game for the Hammers, he would be sent off again, and in total, he would receive 20 red cards over the course of his career.

Stanley Milton

A debut to forget, and seeing as it happened nearly 90 years ago, most people probably have. Until now. Sorry, Stanley.

The goalkeeper made his first start for Halifax Town against Stockport County in January 1934, and promptly conceded a baker’s dozen of goals in a 13-0 defeat, with 11 strikes coming in the second half. To this day, it remains one of the heaviest losses in English footballing history.

Garry Flitcroft

Back to the red cards, and a particularly speedy effort from Blackburn Rovers’ Garry Flitcroft, who lasted just three minutes on his 1996 debut after the referee took exception to him elbowing Everton striker Duncan Ferguson in the face, as referees tend to do.

Flitcroft would go on to enjoy a long career with Rovers, and would eventually become club captain, but as far as first impressions go, this wasn’t great.

Marcos Antonio

So bad that he was substituted after just 16 minutes, Marcos Antonio spent more time on his FC Nurnberg playing through balls to opposition strikers than anything else. An absolute howler gifted VfB Stuttgart an opener inside 30 seconds, and by the time the Brazilian had repeated the feat again just minutes later - albeit without the subsequent punishment of a goal - his new manager had seen enough and gave him the hook.

Warren Barton

Perhaps the only player on this list whose debut was a nightmare for reasons entirely beyond their control. Warren Barton made his England bow against the Republic of Ireland in 1995, but the match was called off shortly before the half hour mark when supporters began to bombard the pitch with projectiles.

What should have been the proudest day of Barton’s career soon descended into absolute chaos, and the defender would only play twice more for the Three Lions.

Lionel Messi

Yep, you read that right. Arguably the greatest footballer of all-time, Lionel Messi endured a brief, hellish debut with Argentina at the age of just 18. The little wizard was introduced as a second-half substitute, ran about for 40 seconds, elbowed a Hungarian, and was shown a straight red card.

In the aftermath, he would state: “It wasn’t the way I dreamed it would be.” Quite the understatement.

Ali Dia

And finally, a special shoutout to the greatest con man the Premier League has ever seen, Ali Dia. After somehow convincing Southampton manager Graeme Souness that he was the cousin of Ballon d’Or winner George Weah, the university student with absolutely no professional footballing experience was handed a top flight debut against Leeds United in 1996.

It quickly became apparent that the Scottish boss had been majorly duped and Dia was subsequently substituted, never to play for the Saints again. If nothing else, you have to admire the gumption of his ruse.