Born in Canning Town, London,[1] Bowyer played for youth team Senrab[3] before joining Charlton Athletic as a schoolboy.

[7] A particular highlight was Bowyer's hat-trick in a memorable 5–4 victory over Wimbledon FC in a League Cup second round first leg tie in September 1995.

[12] Following an incident near a Leeds nightclub in January 2000, in which an Asian student suffered severe injuries, Bowyer and teammate Jonathan Woodgate were charged with causing grievous bodily harm with intent and affray.

A £9 million fee was agreed for a move to Liverpool, which fell through with manager Gérard Houllier not convinced the player had the "hunger or desire" to play for the club.

[24] Claims that Bowyer would have received a £1 million bonus had West Ham stayed up were denied by the club's then manager Glenn Roeder.

[27] In April 2005, Bowyer was in the media spotlight again after an on-pitch brawl with teammate Kieron Dyer in Newcastle United's Premier League match with Aston Villa.

[29] He made 22 appearances in the 2006–07 season,[30] which was disrupted by a dislocated shoulder suffered in West Ham United's 6–0 loss to Reading in January 2007.

[30] He regained a regular place in the Hammers first team at the beginning of the 2007–08 season, scoring his first goals for West Ham against Wigan Athletic and Middlesbrough, and then two more in the 5–0 victory over Derby County.

[35] He scored winning goals in consecutive Premier League matches, against Fulham and Wolverhampton Wanderers, to take Birmingham into a mid-table position at the end of November,[36][37] and was part of the team that went on a run of 15 games unbeaten in all competitions, including a club record 12 unbeaten in the top flight,[38] as they finished in ninth place, the club's best for more than 50 years.

[5] In the absence through injury of Craig Gardner, Bowyer returned to the starting eleven for the match against champions Chelsea in November 2010, and scored the only goal of the game to give his team a surprise victory,[40] and then followed that up with a late equaliser against Manchester United.

[41] In January 2011, television replays highlighted incidents,[42] unnoticed by the match referee, in which Bowyer stamped on Arsenal defender Bacary Sagna and appeared to rake his studs down the same player's Achilles.

Suggestions in the media that Bowyer could receive a six-match ban[43] prompted Birmingham manager Alex McLeish to argue that the football authorities were not treating all clubs equally when using television evidence.

[56] Bowyer's form during the 2000–01 season led to calls for inclusion in the England squad; however, the Football Association ruled that he could not be selected until the court case in relation to an assault on an Asian student was completed.

[57] The FA eventually cleared Bowyer for selection following the conclusion of the court case and England manager Sven-Göran Eriksson called him into the squad for an international friendly against Portugal in September 2002.

[56] In the autumn of 2015, Bowyer spent a month as a guest coach of Watford's under-21 team, working under former Leeds teammate Harry Kewell.

[66] On 14 June, Bowyer was renamed caretaker manager until further notice,[67] and on 6 September, his role was made permanent on a contract lasting until the end of the season.

[68] In Bowyer's first full season at the club, he guided the side to a third-placed finish in League One, and they faced Doncaster Rovers in the play-offs over two legs.

[70] They earned promotion to the Championship by beating Sunderland 2–1 in the play-off final at Wembley Stadium, returning to the second tier of English football after a three-season absence.