In his playing days, Kenny played for Watford Football Club – the only team he represented in his career. His first appearance for the Hornets came against Sunderland in 1980 and he would go on to tally a further 427 games for the North London outfit. He managed 34 goals for Watford.
Jackett was a part of the first Watford side to reach the First Division in 1982. That same year he made his international debut for Wales – a 1-0 win against Norway. Kenny earned 31 caps for his country.
Unfortunately, a string of injuries forced him to prematurely end his career, however Jackett remained at Vicarage Road and joined the coaching team. By 1996, Kenny was First Team Manager.
Graham Taylor took control the following year, but Jackett remained a part of the first team set up, as Watford went on to secure back-to-back promotions to reach the Premier League.
Swansea City: Instant Success
After three years as Ian Holloway’s assistant at QPR and seven years after his first management role, Jackett was appointed Manager of the Swans. In his first season he guided the Welsh side to automatic promotion, finishing third in the fourth division – just three points behind champions Yeovil Town.
In that same campaign, Swansea beat Wrexham to win the FAW Premier Cup.
The following year Swansea finished 6th in League One and marched all the way to the play-off final, ultimately losing to Barnsley on penalties. The Swans retained the Premier Cup and notched their first Football League Trophy for 22 years, beating Carlisle in the final.
Millwall: Promotion & FA Cup Semi-final
Following a brief spell at Manchester City as a reserve Manager, Jackett was hired by the Lions in the November of 2007. His side finished 17th that year, four points above the drop zone.
There was great improvement in his first full campaign, as Millwall reached the play-off final. Former O Gary Alexander fired Jackett’s team 2-1 ahead at half-time, but Scunthorpe came from behind to take the victory.
That defeat was all but forgotten a year late though, when Paul Robinson stabbed home the winner against Swindon, in the play-off final.
Kenny came close to competing in his third play-off in a row the following season but defeat against Barnsley on the final day of the campaign meant the Lions finished 9th.
In the 2012/13 season Kenny led his team back to Wembley, this time for an FA Cup Semi-final against Wigan.
Along the way they beat Preston North End, Aston Villa, Luton Town & Blackburn Rovers, however, the eventual winner of the competition stopped them at the penultimate stage.
League form didn’t quite match the exciting Cup run that season and Jackett resigned from his position in search of a new challenge.
Wolverhampton Wanderers: Record Breaking Season & LMA Manager of the Year
That new challenge would be becoming the new Head Coach of Wolverhampton Wanderers, who were in League One at the time.
Jackett got off to a flyer at his new club winning August’s Manager of the Month after his side went unbeaten in five, winning four.
That form showed no signs of slowing and Wanderers dominated the division, winning 31 matches and recording 103 points – a new record tally for a League One Champion.
After such a successful debut season for his new team, Jackett was awarded the LMA Awards Manager of the Year – a prize that was shared, with Orient’s Russell Slade also getting the nod.
Wolves subsequent return to the Championship was a promising one and Wanderers only missed out on the play-offs on goal difference after registering 78 points.
The 15/16 season would be Jackett’s last in the Midlands, as that summer the club were taken over by their now current owners.
Portsmouth: EFL Trophy Success
Kenny spent a short spell at Rotherham United and in Tottenham’s academy before accepting the job at Portsmouth in the summer of 2017.
In his first season at the Club, Pompey finished 8th, five points off the play-offs. The following year they finished fourth but suffered a 1-0 defeat to Sunderland in the play-off semi-final.
Earlier in the season it was Portsmouth who were victorious, beating the Black Cats on penalties to win the EFL Trophy at Wembley.
The following year Jackett suffered semi-final heartbreak against Oxford having finished 5th in the league. Portsmouth reached the EFL Trophy final for a second consecutive year, but that match was delayed until March 2021 and turned out to be Kenny’s final fixture in charge of the club.
March this year he left his position.
Leyton Orient #BeThere
On the 21st of May 2021, the O’s appointed Jackett as their new First Team Manager.