John Oster

Grimsby Town

Oster started his career at Grimsby Town and had progressed through the youth ranks at the club and was inducted into the first team in the same youth squad as players such as Danny Butterfield, Matthew Bloomer and Daryl Clare. He was promoted to the first team scene in the 1994–95 season when the club were in the old First Division. However, he didn't make his debut until the 1996–97 campaign where he made his debut in a 3–1 win away at Charlton Athletic on 26 November 1996. Following Grimsby's relegation from the First Division, Oster was sold by The Mariners, for a fee of £1.5 million that saw him break the club's record transfer sale that was initially held by Gary Croft following his move to Blackburn Rovers for £1 million a year earlier. He had only played twenty-six times in all competitions, scoring four goals upon his departure.

Everton

The Mariners sold Oster to Everton for £1.5 million in 1997, aged only 18 and having played only 25 matches. It transpired that he had made the wrong move though, as he was rarely utilised in his favoured winger's role, in a 4–4–2 formation. Oster scored three times during his spell at Everton; once in the league against Barnsley, once in the League Cup against Scunthorpe United and once in the FA Cup against Coventry City.

Sunderland

Oster moved to Sunderland for a fee in excess of £1 million, but again failed to find regular form. His low point at the club was when he was involved in an…

Oster made his debut for Wales as an 18-year-old in 1997, coming on as an injury-time substitute for Robbie Savage in a World Cup qualifying defeat in Belgium. Oster played intermittently for the national side between 1997 and 2004, accumulating 13 caps, though only six of these came in competitive games. Oster did not play in any games under John Toshack following his appointment in November 2004, his last cap for Wales being the 2–2 draw with Northern Ireland in 2004 under previous boss Mark Hughes.

In September 2019, Oster was appointed as assistant manager of Whickham under manager Matty Pattison. The duo resigned from their position on 1 February 2020.

In April 2002 whilst at Sunderland, Oster accidentally shot reserve team player Mark Maley with an air-gun. Neither of the pair believed the gun was loaded and Maley had to undergo an eye operation. Whilst on loan at Leeds United in December 2004 Oster and Jamie McMaster were suspended by the club for misbehaving at the club's Christmas party. The incident spelled the end of his Leeds career and his loan was terminated. In 2005 his Sunderland contract was terminated after he was arrested for assault outside a Durham nightclub.