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On 13 May 2018, after receiving his seventh title as a player, Simons announced that he is putting an end to his active playing career. He received a wildcard from the board of Club Brugge, meaning he can take up a position in the future in the context of the club.

After his non-selection for the 2014 World Cup, Simons' international career seemed over. Prior to the first international match after this World Cup (a friendly match against Australia ) he was honoured alongside Daniel Van Buyten for their merits with the national team. On 13 November 2016 Simons was called for the international match against Estonia, after the injury of Kabasele. In that match, he came on for seven minutes. This made him. at 39 years, 11 months and 2 days the oldest Red Devil ever in an official competition.

He is the fifth-most capped player of all time in the Belgium national football team (after Jan Vertonghen, Axel Witsel, Eden Hazard and Jan Ceulemans), having earned 94 caps. He became the oldest capped player when, at age 39, 11 months and 2 days, he played against Estonia on 13 November 2016.

On 12 June 2013, Simons signed a two-year contract with the option of staying in a technical position at Club Brugge. During the first match of the 2013/14 season, Simons made his comeback for the club. He got a questionable red card on matchday 1 after 21 minutes after a foul on Charleroi player Ederson. On 15 May 2016, as captain, he lifted the Belgian title in the air after a 4-0 victory against RSC Anderlecht. He played his 1000th match as a professional football player against AA Gent on 29 January 2017. The club lost that match 2-0.

With his new German team, Simons became very important, both with his leadership qualities and his great playing ability. For two seasons Simons was the player who played the most in the Bundesliga. In the 2010-2011 season, he did not miss a minute. Because of his excellent results, he came to the attention of his old Club Brugge team but also of Anderlecht. Simons quieted those speculations by extending his contract until 2014. In three season with Nürnberg, he finished 6th, 10th and 10th in the Bundesliga

In PSV's game against Willem II on 6 October 2007, the PSV fans showed their affection towards Simons. The entire West stand was wrapped in the Belgian flag and a banner was unfurled with the text: "Captain Simons: Our Lion of Flanders". Simons once again became champion of the Netherlands with PSV in the 2007/2008 season. His fourth title in a row. He scored four times in the 2007/2008 season. Together with goalkeeper Heurelho Gomes, Simons played the most minutes for PSV, they both missed only one league game and played the other 33 from the beginning to the end. The defensive midfielder got a solitarily yellow card and not a red card, in the UEFA Cup match against Tottenham Hotspur, he received a yellow card, raising the total amount to 6 yellow cards in 140 official matches for PSV in his first three seasons.

In his second year at PSV, Simons was once again an integral part of PSV. Of the total 49 matches that PSV played in the domestic league, Champions League, Super Cup and Cup, Simons played 48. Each time, he played the full 90 minutes, becoming an important part of the 2006/2007 championship-winning side. After the departure of Phillip Cocu, he was appointed the captain of PSV in the 2007/2008 season.

Simons was signed from Club Brugge on 29 June 2005, succeeding Mark van Bommel, who left for Barcelona. Before Simons went to PSV, he also negotiated with Feyenoord, on the advice of Bart Goor. Feyenoord, however, found difficult to meet the asking price and moved the transfer on the long-term after the resignation of head coach Ruud Gullit. Club Brugge, therefore, stopped the negotiations. Simons immediately won a starting place at PSV. With PSV he became champion of the Netherlands in the season 2005/2006. Simons soon became the penalty taker of PSV, as he had previously at Club Brugge. In the Eredivisie match against NAC Breda, he missed one of his first penalties in his career. Timmy Simons commented: "It was good that it was a wrong penalty, I still have some peace with it".

Simons made his debut on 30 April 2001 for the national team of Belgium in a friendly match in and against the Czech Republic, alongside Peter Van der Heyden. At the national team he was a fixture and under coach René Vandereycken he became captain. But under Dick Advocaat he was pushed aside. Frome his first team selection the "somewhat older" Simons was dropped. And the matches after that Advocaat did not call back Simons either. From 2001 to 2011, Simons collected 88 caps. He was called back under national coach Georges Leekens and also under the reign of Marc Wilmots.

Simons' career started with KTH Diest, the team where he received his training. In 1998 he left for first division Lommel SK, where he quickly established himself in the first team. After a strong second season at Lommel, he moved to Club Brugge in 2000. Simons immediately forced a place in the first team in the 2000/2001 season. He grew into a fixture at this Belgian club in no time, quickly growing into the team's penalty taker and, after a few seasons, the captain. In 2002 he was also named as player of the season. With Club Brugge, he became a 2-time Belgian national champion and won the Belgian Cup on two occasions.

Timmy Simons (born 11 December 1976) is a former Belgian professional footballer who last played for Club Brugge in the Belgian Pro League. He played as a defensive midfielder, and is known for his tireless work ethic and penalty-taking ability, having scored 48 competitive goals through penalty, missing only 5. In 2012, at age 36, Simons was both the outfield player with the most minutes and the most kilometres in the Bundesliga. Simons' former clubs include Lommel, Club Brugge, PSV Eindhoven and 1. FC Nürnberg. He has captained both Club Brugge and PSV Eindhoven, and won the Belgian Golden Shoe in 2002 while playing for Club Brugge.