Biggest regrets? Michael Owen picks two tournaments England’s ‘Golden Generation’ of David Beckham & Co should have won

Owen burst onto the scene with England in 1998 - becoming their youngest tournament goalscorer as an 18-year-old at that summer’s World Cup, before recording a legendary effort against Argentina in the last 16. Said contest ended in penalty shootout heartache, with the Three Lions having been reduced to 10 men on the back of David Beckham’s infamous red card.

With Sven-Goran Eriksson at the helm by 2002, England boasted a star-studded squad that included the likes of Owen, Beckham, Ashley Cole and Steven Gerrard. Ronaldinho and Brazil dashed more World Cup dreams, before Frank Lampard and Wayne Rooney were added to the pot for a European Championship bid in 2004 - which delivered more penalty pain against Portugal. Cristiano Ronaldo, and his iconic wink, was at it again two years later in 2006.

Having never been able to turn potential into some more tangible, which of the aforementioned heartbreaking events left Owen most disillusioned and cursing the fact that a winners’ medal was not secured?

Reacting to that question, the man himself - who is UK ambassador for the online casino comparison site Casino.org - told GOAL: “Oh God! Well, I played in five major tournaments. The one that I always think we had our best team - but I don't lie awake thinking, ‘Oh, we should have won it’ - 2002 in Japan, we got beat by the eventual champions, but that was a very, very good team.

“We basically needed to beat one team. On the other side of the draw, you had Germany, who we had just beaten 5-1. You had Turkey and South Korea and it opened up on the other side. But we had Brazil on our side, which was the nightmare. I do almost think we were one game there away from winning it.

“98, everything that could go wrong went wrong. We had a red card, we lost on penalties, we had a perfectly good goal disallowed against Argentina. We really should have gone through that. Who knows how far we would have gone in 98.

“2006, I got injured halfway through and no real strong view. Even Portugal, when we played in Portugal, we should have beaten Portugal. Wazza [Rooney] got injured after 15 minutes or whatever. We were 1-0 up. That could have been Greece in the final. That was another one.

“I'd say probably Portugal and Japan, they were the two tournaments that I really think we could have won.”

Gareth Southgate looked like being the man that could get England back over the winning line during a tenure that resulted in him becoming a ‘Sir’ and knight of the realm, but semi-final and final setbacks were suffered in World Cup and Euros competition.

Thomas Tuchel is the latest to pick up that managerial baton, with the former Bayern Munich and Chelsea boss boasting domestic and Champions League titles on his distinguished coaching CV.

He has raised a few eyebrows with his selection for the 2026 World Cup - with the likes of Cole Palmer, Phil Foden, Harry Maguire and Trent Alexander-Arnold being overlooked - but boasts steadfast belief in his ability to deliver where the Golden Generation failed, with inspiration being taken from the near misses that Owen and Co once endured.