Steve McClaren, the former England manager, faced another setback in his career as his Jamaican team failed to secure a spot in the World Cup finals, losing out to the small island nation of Curacao, which made history as the smallest nation to qualify for the tournament.

Renowned for his unfortunate moniker, “the Wally with the brolly,” McClaren first gained notoriety when England, under his leadership, did not qualify for Euro 2008 after a memorable rainy defeat to Croatia at Wembley.

Now, in the Caribbean, McClaren has resigned from his position following Jamaica’s inability to qualify, drawing 0-0 with the underdog Curacao. This result leaves the Jamaican team, known as the Reggae Boyz, facing a play-off tournament in hopes of securing a place at next summer’s World Cup.

In a statement, McClaren acknowledged the challenges, saying, “Football is a results business, and tonight we have not achieved our objective of advancing from this group.”

He continued, “It falls upon the leader to accept responsibility, make crucial decisions, and act in the team’s best interest. After thorough reflection and a candid evaluation of our current state and future needs, I have chosen to resign as head coach of the Jamaican national team.”

Steve McClaren has quit as Jamaica manager after failing to qualify them for the World Cup

The Reggae Boyz were held to a dismal 0-0 draw in Kingston by minnows Curacao, who have qualified for their first ever major tournament – while Jamaica will now head to the play-offs

‘After deep reflection and an honest assessment of where we are and where we need to go, I have decided to step down as head coach of the Jamaican national team.’

He added: ‘Sometimes the best thing a leader can do is to recognise when a fresh voice, new energy and a different perspective is required to move this team forward. I’m positive this team will succeed in March.

‘I thank you, Jamaica. I will be forever grateful to have led the Reggae Boyz, really has been an honour, respect and one love to you all.’

Michael Ricketts, President of the Jamaica Football Federation, delivered a blunt assessment. 

‘To say I’m disappointed is an understatement. We engaged Heimir Hallgrimsson, then he left, we thought Steve McClaren would have been a good replacement, it has turned out that he has not been such a good replacement. We are supremely disappointed,’ he said.

‘We will reorganise, we have a second bite of the cherry, we will put things together and of course have an emergency meeting with the technical staff, and we will put an interim coach in place.’

According to the tiny nation’s assistant manager Dean Gorre, stepping in for Dick Advocaat, it brought McClaren to tears. ‘Steve was crying,’ he said. ‘It affected him that much.

McClaren only took over as Jamaica boss after leaving Manchester United, where he was assistant manager to Erik ten Hag, in the summer of 2024.

There was joy for Curacao, who are headed to the World Cup for the first time ever

The tiny Caribbean nation became the smallest country to ever qualify for the tournament

With the three Concacaf giants – USA, Mexico and Canada – already qualified for next year’s tournament by virtue of being the host nations, this was seen as a golden opportunity for Jamaica to secure their spot at only their second World Cup. Their sole appearance having been at France ’98, when they finished third in their group and failed to advance to the knockout stages.

But not even a rousing pre-match speech from the island’s most famous son – Usain Bolt, the fastest man of all time – could help McClaren’s side from limping to a goalless draw in Kingston.

Instead, the night belonged to Curacao. They became the smallest nation by population to qualify for a World Cup and will be joined by CONCACAF sides Panama and Haiti who also booked their spots.

Curacao, 37 miles off the Venezuela coast, only became a country within the Kingdom of the Netherlands in 2010, following the dissolution of the Netherlands Antilles. Ten years ago they were 150th in Fifa’s world rankings. They are now 82nd.

They finished as the only undefeated nation in the tournament and finished atop of Group B with 12 points to advance to the World Cup for the first time in its history.

There was further embarrassment for McClaren, given Curacao secured the historic result despite not having his opposite Advocaat on the bench. The 78-year-old manager missed the crucial match because he had to return to the Netherlands last weekend for family reasons.

Advocaat was at the helm of the Netherlands national team for three stints and managed South Korea, Belgium and Russia before taking the job with Curacao, and will become the oldest coach at a World Cup – beating Otto Rehhagel’s record when he was in charge of Greece aged 71 in 2010.

With the three Concacaf giants – USA, Mexico and Canada – qualified for next year’s World Cup by virtue of being the hosts, this was seen as a golden opportunity for Jamaica to go through

According to the Central Bureau of Statistics in Curacao, the country has a population of 156,115 persons as of last January – similar to the size of Cambridge or Huddersfield

According to the Central Bureau of Statistics in Curacao, the country has a population of 156,115 persons as of last January – similar to the size of Cambridge or Huddersfield. Iceland, with a population of just over 350,000 was the smallest country to reach the World Cup when it qualified for the tournament in Russia in 2018.

Panama advanced to its second World Cup after defeating El Salvador 3-0 on first-half goals from César Blackman and Erick Davis. Jose Luis Rodriguez added a goal for the Panamanians, who have Russia 2018 as their only World Cup appearance.