Darryl Flahavan

Southampton

Flahavan began his career at Southampton. He was named as an unused substitute several times in the Premier League, but did not make a first team appearance, being behind Paul Jones, Dave Beasant and Maik Taylor in the pecking order. He left Saints on a free transfer in 1998, and went on to make his name with Conference side Woking.

Southend United

He was signed by Southend in October 2000. Flahavan played for Southend during two spells and in total made 356 appearances for the club helping them from League Two into the Championship in back-to-back seasons. Flahavan was seen as one of the main reasons behind the club's rise through the divisions. Flahavan put in a man of the match display against Manchester United in the League Cup on 7 November 2006, making a string of saves from Cristiano Ronaldo and Wayne Rooney. Southend won the game 1–0 with a Freddy Eastwood free kick. Southend were eventually knocked out the competition in the quarter-finals to Tottenham Hotspur at White Hart Lane 1–0 where again Flahavan produced another man of the match display.

Crystal Palace

Flahavan signed for Championship side Crystal Palace in early July 2008 on a Bosman ruling free transfer, signing a three-year contract to compete for the first team shirt with Julián Speroni. He rejected Southend's offer of a one-year deal. Flahavan made his debut in Palace's 2–1 League Cup win over Hereford United in August 2008. Flahavan also played in the next round…

On 13 June 2016, Flahavan retired from playing when he was appointed the goalkeeper coach of Leeds United as part of the backroom staff to new head coach Garry Monk. Flahavan had a loan spell at Leeds during his playing days and was a former teammate of Monk during his Southampton days. On 21 June 2017, Flahavan followed Monk to Middlesbrough after Monk resigned as Leeds manager Flahavan was appointed goalkeeping coach of EFL Championship club Birmingham City when Monk took over as manager on 4 March 2018. On 12 August 2020, he joined Sheffield Wednesday as their goalkeeper coach. He left the club on 9 November 2020, when Garry Monk left the club. On 25 June 2021, he joined Wigan Athletic as the goalkeeping coach. On 9 October 2023, Gary White, head coach of Chinese Taipei, mentioned in an interview that Flahavan has been appointed as the new goalkeeper coach of the national team. In his first game, Chinese Taipei took a brilliant 4-0 win against Timor Leste. On 18 January 2024, he joined Plymouth Argyle as first team goalkeeping coach. On 3 October 2025, Flahavan rejoined Sheffield Wednesday as their goalkeeper coach for a second time.

Flahavan was born in Southampton. Flahavan's older brother Aaron was also a professional football goalkeeper. He played for Portsmouth before dying in a car crash in 2001. Darryl has a son, named Aaron in memory of his brother, who is also a goalkeeper who plays for Bedford Town FC.

Southend United

Football League One: 2005–06 Football League Two play-offs: 2005 Football League Trophy runner-up: 2003–04, 2004–05 Individual

PFA Fans' Player of the Year: 2005–06 League One PFA Team of the Year: 2005–06 Football League One