Greening began his career in 1996 with York City, but moved to Manchester United in 1998, with whom he won the 1998–99 UEFA Champions League as a non-playing substitute in the final. However, he failed to make a breakthrough in the Manchester United first team and followed United assistant manager Steve McClaren to Middlesbrough in 2001. During his time at Middlesbrough, Greening earned his first call-up to the England national team, but he did not make an appearance. In 2004, he joined West Bromwich Albion for £1.25 million, and, in 2008, captained the team to the Championship title. Greening signed for Fulham in 2009 and helped them to the 2010 UEFA Europa League Final, before signing permanently the following summer. He signed for Nottingham Forest in 2011 and had a three-year spell with the club.
Born in Scarborough, North Yorkshire, Greening joined the York City youth system at the age of 15. He signed with the club's Youth Training Scheme in December 1996 and broke into the first team towards the end of the 1996–97 season, making his debut as substitute in a 1–1 draw away to Bournemouth on 22 March 1997.
Following a four-day trial with Manchester United in February, he signed for the Premier League team on 25 March 1998 for what was understood to be an initial fee of £500,000, which could have potentially risen to £2 million dependent on appearances and international recognition, with a sell-on clause. He later admitted that he signed for United on £400 a week without looking at the contract. As an attacking midfielder, he faced massive competition from more established players in both positions and his first-team opportunities were restricted, although he did make the substitute's bench in the 1999 UEFA Champions League Final. He later admitted that he "felt a bit of a fraud" for picking up his winner's medal, having not played a single minute of European football that season. He did however make a contribution to their victorious FA Cup campaign, coming on as a substitute at half-time in their fifth round tie with future club Fulham.
Greening signed a new contract with United at the end of 1999–2000, but by 2001 he had become frustrated by the lack of first-team opportunities, and conceded that he would need to leave the club in order to play regularly.
On 9 August 2001, Greening joined Middlesbrough for a combined fee of £3 million which saw both him and United teammate Mark Wilson head to Teesside to rejoin former Manchester United assistant manager Steve McClaren, who was by now the manager of Middlesbrough. Greening remained on Teesside for three seasons, being voted Club Player of the Year for 2002–03 and also being selected for the full England squad (though he did not play). But his first-team chances were more limited during 2003–04, after which he signed for West Bromwich Albion for an initial fee of £1.25 million. Greening was part of Middlesbrough's 2004 League Cup-winning team, despite not making the squad for the final.
West Bromwich Albion
Greening made his Albion debut in a 1–1 draw away to Blackburn Rovers on the opening day of the 2004–05 Premier League season, and quickly established himself as a key player in the Baggies' midfield, helping to secure their Premier League survival in his first season. He was named Albion's Player of the Year in 2005–06, in which he made 41 appearances and scored 2 goals as the club was relegated to the Championship.
He signed a new three-year contract with Albion in August 2007, and was made club captain for 2007–08. His performances during the campaign led to him being named in the Championship Team of the Week on several occasions. Greening missed the fifth round FA Cup match at Coventry City due to suspension, but it was the only match he missed during the campaign; he started all 46 league matches and also participated in eight out of nine cup games. He captained Albion in the FA Cup semi-final, where they lost 1–0 to Portsmouth, and one month later led the team to promotion as winners of the Championship. Greening was named in the 2007–08 Championship PFA Team of the Year, alongside teammates Paul Robinson and Kevin Phillips. During the last two months of the season Greening suffered from a double hernia problem but played on until the end of the campaign, when he had an operation to rectify the injury.
Towards the end of 2008–09, Greening said he was looking to sign a new contract with Albion. He was offered a new four-year contract by the club, but instead handed in a transfer request in July 2009.
On 14 July 2009, West Brom rejected a "derisory" bid from Fulham for Greening. Nevertheless, on 24 August 2009, Greening joined Fulham on a season-long loan for 2009–10, with a view to a permanent move upon completion of the loan period. He scored his first and only league goal for Fulham against Portsmouth on 3 February 2010. He also came off the bench in the 2010 UEFA Europa League Final defeat against Atlético Madrid.
Greening signed a two-year contract with Fulham on 1 July 2010 after a successful loan spell the previous season. After signing, he was mainly used as a substitute and was seen as a 'fringe' player. Under new manager Mark Hughes, he rarely featured, making only 10 league appearances in 2010–11.
On 18 July 2011, Greening signed a three-year contract with Championship club Nottingham Forest for an undisclosed fee, reuniting with manager Steve McClaren for the second time after working with him at both Manchester United and Middlesbrough. Greening said the move met his desire to seek regular football. He took up a coaching role with Forest's under-21 team in July 2013, after attaining UEFA 'B' and 'A' Licences over the summer. Greening made 13 appearances for Forest in 2013–14 before being released by the club in May 2014.
Greening made his only appearance for the England national under-18 team as a substitute for Danny Cadamarteri in a 1–0 home defeat to France on 23 April 1998. His first cap for the under-21 team came after starting the 2–2 away draw with Hungary on 27 April 1999, with his first goal coming in the 61st minute of a 6–1 home win over Georgia on 31 August 2000. Greening was drafted into the England squad for the 2002 UEFA European Under-21 Championship as a replacement for the injured Michael Carrick, two days prior to their first match of the tournament. He played in the final Group A match, a 3–1 loss to Portugal on 22 May 2002, with England being eliminated from the tournament after finishing bottom of Group A. This proved to be the final of his 17 appearances for the under-21s, for whom he scored three goals. Greening was also called up to the full England squad by Sven Goran Eriksson but failed to make an appearance.
Style of play
Although naturally right-sided, Greening can operate anywhere across the midfield. Initially an attacking wide midfielder, he later moved to a central midfield holding role. Teammate Dean Kiely once described how Greening "sprays passes around like a quarterback" in Albion's style of attacking football under Tony Mowbray.
Greening began assisting with coaching the Academy team of his former club York, then in League Two, during the summer of 2014, before retiring from playing professionally during September 2014. He signed for Northern Counties East League Premier Division club Tadcaster Albion on 19 September 2014, where his younger brother Josh played, making his debut the next day in a 6–0 away win over Maltby Main. Greening was appointed as Development Phase Coach at York's Academy on 22 December 2014, a role focusing on the development of the team's players aged 16 to 18.
He registered as a player with York on non-contract terms on 13 November 2015, to provide cover with a number of midfielders unavailable. His second York debut came two days later as a half-time substitute for Rhys Turner in a 2–1 home defeat to Plymouth Argyle; according to The Press, he "inspired an improved second-half display ". Greening was sent off for violent conduct after elbowing Michael Doyle on his third appearance, in a 6–0 away defeat to Portsmouth on 24 November 2015, for which he received a three-match suspension. He left the club by mutual consent on 16 December 2015, despite offering only days earlier to carry on playing for the rest of 2015–16. Greening rejoined Tadcaster on 30 December 2015. He made 21 appearances and scored one goal in 2015–16 as Tadcaster won the Northern Counties East League Premier Division title, and thus promotion to the Northern Premier League Division One North.
West Bromwich Albion
- Denzil Haroun Reserve Team Player of the Year: 1999–2000
- West Bromwich Albion Player of the Year: 2005–06
- PFA Team of the Year (Football League Championship): 2007–08
- Jonathan Greening at Soccerbase