Youth

Born in Rotterdam, Drenthe, who is of Surinamese descent, joined local side Feyenoord's youth system at the age of 13, playing mainly as a winger during his junior years. After disciplinary issues during a trip to Switzerland with the B-side, coach Marcel Bout wanted him to leave the club, but the issues were resolved after the intervention of Rob Baan, the club's director of football.

Bout hardly used Drenthe in his subsequent lineups, and, at the end of the season, the 16-year-old was named as one of eleven players whose future at the club was questionable. He eventually moved to Feyenoord feeder club Excelsior.

Drenthe improved during the two years he played at Excelsior, with manager Marco van Lochem successfully playing him as left back. After impressing his former side's coaching staff, he was asked to rejoin the club, which he accepted.

Feyenoord

In the 2005–06 season, Drenthe was promoted to Feyenoord's first team, managed by his former youth coach Henk Fräser. After scoring three goals against Ajax in the Otten Cup youth tournament he began training with the main squad, while still appearing for the reserves.^{[citation needed]}

In the same week where he helped his club to a 5–1 win at Ajax with the second team, Drenthe was offered a professional contract at Feyenoord. Manager Erwin Koeman handed him his Eredivisie debut against Vitesse at the Gelredome, and the player finished the season with three matches.

In 2006–07, Feyenoord signed veteran Belgian Philippe Léonard, while Pascal Bosschaart was also still part of the squad. After the former suffered an injury and the latter was transferred to ADO Den Haag, Drenthe became first-choice as Feyenoord finished seventh in the league.

After winning the 2007 UEFA European Under-21 Championship with the Netherlands, Feyenoord accepted a €14 million bid by Real Madrid after Drenthe threatened to take his club to court if they did not want to let him go.^[6][7][8]

Real Madrid

Drenthe was presented as a Real Madrid player on 13 August 2007, alongside compatriot Wesley Sneijder. He made his official debut as a midfielder in the second leg of the season's Spanish Supercup against Sevilla, and scored the 1–1 equaliser from 40 yards out, with the ball hitting the crossbar and crossing the line. The Merengues, however, lost 3–5 at home and 3–6 on aggregate.^{[citation needed]}

Drenthe played regularly for Real Madrid in his debut season, in both left-wing positions, but began appearing less after the development of Marcelo, being dropped from the list of 18 by manager Bernd Schuster in several games. At one time, after being left out for the match against Valencia, Drenthe stormed out of the training ground. He finished the campaign with 18 league appearances (plus four in the season's UEFA Champions League), scoring his first league goal against Real Valladolid in a 7–0 home routing on 10 February 2008. ^{[citation needed]}

Despite rumours of him leaving the club on loan, Drenthe featured in 15 of Real Madrid's first 18 games of the 2008–09 season. However, he also suffered from anxiety issues after being booed by the club's supporters during a 1–0 home win against Deportivo de La Coruña and did not feature for the club for a period, although manager Juande Ramos offered the player his support and insisted he would help him.^[9] The manager later revealed that the player asked not to be picked for the three games after the Deportivo fixture.^[10]

On 31 August 2010, after having appeared rarely in his third season, Drenthe was loaned to Hércules in a season-long move.^[11] He made his debut on 11 September in a 2–0 away win against Barcelona,^[12] and scored his first goal for the club on 14 November, netting from a free kick against Real Sociedad in a 2–1 home victory.^[13] His performances with the Alicante team were subsequently praised by the Spanish press.^[14] However, the player would soon fall out of favour with the club's board of directors and coaching staff after arriving one week after the winter break ended, citing a "loss of confidence in Hércules management", rather than what was previously perceived as "a protest over unpaid wages".^[15]

On 3 April 2011, in his second game after his suspension, Drenthe scored twice to help Hércules to its first away win since September, a 3–1 against Real Sociedad.^[16] He ended the season with 15 starts in 1,299 minutes of action, with his team being finally relegated. ^{[citation needed]}

Everton

On 31 August 2011, Drenthe joined Premier League club Everton on a season-long loan deal.^[17] He made his Premier League debut as a second-half substitute in the 2–2 home draw against Aston Villa, on 10 September. Again from the bench, against Wigan Athletic, he scored in the 97th minute to round off a 3–1 home victory.^[18][19]

Drenthe made his first start for Everton on 21 September 2011 in a League Cup match against West Bromwich Albion, assisting the winning goal for Phil Neville in the 13th minute of extra time (2–1 home win).^[20] On his full league debut, at Fulham on 23 October, he found the net just three minutes into the game in an eventual 3–1 win.^[21]

On 21 December 2011, after three weeks out of the game due to an ankle injury, Drenthe assisted Leon Osman for the game's only goal at home against Swansea City.^[22] On 18 February 2012, in a match against Blackpool for the season's FA Cup, he scored after just 49 seconds in a 2–0 home success.^[23] Drenthe started in the next game for Everton, scoring a powerful low drive from 20 yards out for the first goal of the 1–1 away draw against Queens Park Rangers.^[24]

In March 2012, Drenthe was given a leave of absence on compassionate grounds and, upon returning, he reported late for training. This resulted in manager David Moyes omitting the player from Everton's FA Cup semi-final squad; he was also told to stay away from the club.^[25] Former Everton Goalkeeper Tim Howard confirmed that poor discipline and attitude around the club played its part in Drenthe being left out the squad. ^[26]

In a magazine interview published in April, he accused Barcelona's Lionel Messi of racially abusing him on more than one occasion, repeatedly addressing him as "negro".^[27]

Alania Vladikavkaz

Drenthe left Real Madrid after his contract expired on 30 June 2012.^[28] In December, he signed a deal with Russian club Alania Vladikavkaz, which came into effect on 2 February of the following year.^[29] Drenthe made his league debut for his new team on 9 March 2013, against Rostov. After the game, coach Valery Gazzaev called him a "great professional and an example for the youth".^[30] On 15 April, in only his fifth game for the club, he scored a hat-trick in a 3–1 home win over relegation competitors Mordovia Saransk.

Reading

Reading officially confirmed the signing of free agent Drenthe on a two-year contract with the option of a third, on 21 June 2013.^[31] On 8 March 2014, Drenthe scored his first goal for the club in a 1–1 draw away at Brighton & Hove Albion after he cut in from the right and fired a left-footed shot into the bottom corner. Drenthe then scored his second goal for the club on 11 March in a 4–2 away win against Leeds United with a free-kick just after half-time. In July 2014, Drenthe was told he could leave Reading after only one season with the club,^[32] whilst being stripped of his squad number when the official squad numbers were announced on 14 July 2014.^[33]

Sheffield Wednesday

Drenthe joined Sheffield Wednesday on a six-month loan on 1 September 2014, halfway through transfer deadline day.^[34] He made his Owls debut as a second-half substitute for Chris Maguire in the 0–0 away draw against Bolton Wanderers on 13 September. His only Owls goal came in the 1–1 away draw at Charlton Athletic on 1 November.

Kayseri Erciyesspor

On 23 January 2015, Drenthe joined Turkish Süper Lig side Kayseri Erciyesspor.^[35]

Baniyas

Drenthe joined UAE Pro League side Baniyas Club in September 2015.^[36] He was released in July 2016.^[37]

Hiatus

Unable to find a club, Drenthe announced a hiatus from professional football, saying that he was 'no longer a footballer'.^[38]

Sparta

After training with the side for a few weeks, on 6 July 2018 Sparta Rotterdam announced they had signed Drenthe to a one-year deal.^[5] After Sparta Rotterdam promoted to the Eredivisie during the Keukenkampioen 2018–2019 season, the club decided not to extend his contract.^[39]

Kozakken Boys

Drenthe then signed for Kozakken Boys.^[40]

Return to Spain

On 6 January 2021, Drenthe returned to Spain and signed with Racing Murcia.^[41] On 30 January 2022, Drenthe was loaned to Real Murcia, playing in the same city but a tier above Racing.^[42] In August 2022, he joined Racing Mérida City in the sixth-tier Primera División Extremeña.^[43]

Return to Kozakken Boys

At the end of 2022 he returned to Kozakken Boys on a try-out.^[44]

On 17 November 2023, Drenthe announced his retirement from professional football.^[45]

As TV commentator

Drenthe was contracted by the Spanish sports program El Chiringuito de Jugones as commentator, on 1 March 2021.^[57]