Named the 1997 Dutch Football Talent of the Year, Zenden played for four teams in the English Premier League, totalling 180 games and 19 goals.

Internationally, Zenden earned 54 caps and scored seven goals for the Netherlands, whom he represented at two UEFA European Championships and the 1998 FIFA World Cup.

[8] As his career developed at PSV, Zenden made the left wing position his own, displacing Peter Hoekstra and finally becoming a firm member of the starting line-up after the departure of Dutch national team player Jan Wouters.

Zenden was an important part of the PSV team that won the Eredivisie championship in 1996–97, where he also received the 1997 Dutch Talent of the Year award.

He found his first-team opportunities at Barcelona limited by the form of fellow Dutchman Marc Overmars, however, who played in Zenden's favoured left wing position for both club and country.

Instead, Zenden was deployed as a left wing-back, a defensive role which he took on successfully, as he displaced Spanish international and local favourite Sergi.

[10] In his two years at Chelsea, Zenden played in the 2002 FA Cup final, a 2–0 defeat to Arsenal; however, he struggled to maintain a constant place in the starting line-up mainly due to persistent injuries.

Here he found playing success, as he scored the winning goal in the 2004 League Cup final against Bolton Wanderers to secure Middlesbrough their first major trophy in club history.

[12] He was deployed in a central midfield position, where he played 36 of 38 league games, scoring five goals in the process, and was voted the Middlesbrough fans' 2005 Player of the Year.

[citation needed] After being released, Zenden revealed that he wanted to end his career in England, with Blackburn Rovers and Portsmouth interested in the player.

[21] Zenden signed in time to make his debut against former club Liverpool and he did an excellent job helping Sunderland to retain their one-goal lead after coming on as a substitute for the injured Lee Cattermole.

[28] On 22 May 2011, his last game for Sunderland, he scored the opening goal in a 3–0 win over already-relegated West Ham on the final day of the 2010–11 Premier League season.

[citation needed] Zenden made his debut for the Netherlands national team in a 1998 FIFA World Cup qualification match against San Marino on 30 April 1997.

His man of the match performance in a friendly against Germany at the turn of the millennium cemented his position in the national team – he set up the opening goal for Patrick Kluivert, then added his own name to the scoresheet with a thunderous volley from Ronald de Boer's corner, before nearly putting the gloss on the finish when he left the entire German defence for dead with his raw pace, beat the goalkeeper with his shot, only for it to rebound off the upright.