[2] Born in Southend-on-Sea, Essex, Lockwood was a trainee with his hometown club, Southend United, before signing a professional contract with Queens Park Rangers on 2 May 1995.
[1] Lockwood was part of the successful QPR reserve team that won the Avon Combination league in the 1995–96 season.
After completing his contract with Bristol Rovers, Lockwood moved on a free transfer to Leyton Orient, where he became an integral part of the first team.
[4] Later, when Lockwood attracted the attention of Championship clubs, including Millwall,[5] West Bromwich Albion,[6] and Crystal Palace,[7] Leyton Orient offered him an improved two-year deal, which he signed at the end of the season.
[12] During the 2001–02 season, Lockwood suffered a significant spleen injury during a match against York City in August 2001 after colliding with an opposing player.
He made his return in a match against Crystal Palace reserves, stating: "It was great to be back, and the management felt I did well and are pleased with my progress ...
"[14] In July 2007, Lockwood signed for League One giants Nottingham Forest for an undisclosed fee, agreeing to a two-year contract.
Orient manager Martin Ling said, "He's been very close to signing for top-flight teams in the past, and I think he felt at this stage of his career it was too good an opportunity to turn down.
[22] After departing, he was linked with a return to Colchester under new manager John Ward, but he refused, describing his time there as a "nightmare.
Lockwood spoke out about the club's administration, stating that the team was determined to stay up against all odds, despite being deducted 25 points in the league.
The following season, Lockwood scored in the opening game against Partick Thistle, helping Dundee secure a 1–0 victory.
Three months later, he scored his first goal of the season with a trademark free kick that flew into the top corner, securing a 1–0 win for Dundee against Heart of Midlothian.
[33] Following Dundee's relegation, Lockwood signed a new one-year deal, having impressed new manager John Brown by playing at left-back, centre-back, and as a sweeper towards the end of the previous season.
[41] Source:[42][43] In 2023, Lockwood was appointed head coach and technical director of the Montserrat national football team.
[44][45] He managed only two games in March 2023 before being replaced by Lee Bowyer for the team's September fixtures,[46] while continuing in his role as technical director.