Born in Torres Novas, Santarém District, Casquilha played 19 years as a senior. He started out at local Clube Desportivo Torres Novas, then alternated between the second and third divisions in the following seasons. Casquilha made his debut in the Primeira Liga in the 1999–2000 campaign, aged already 30: alongside future S.L. Benfica and Portugal star Petit, he was an essential midfield unit for Gil Vicente F.C. who finished a best-ever fifth position, scoring three goals in 32 games. After helping the Barcelos club always retain its league status, and having amassed totals in the Portuguese top flight of 177 matches and 11 goals, 36-year-old Casquilha left and signed for S.C. Espinho in the third level, following which he retired.
Coaching career
Casquilha began coaching in 2006, immediately after retiring. He started with amateurs Santa Maria FC, which he guided to the second place in the AF Braga regional championships. In quick succession, he then worked with Merelinense F.C. and C.A. Valdevez, guiding the latter to the last 16 in the Taça de Portugal in 2007–08. In summer 2009, Casquilha was appointed at Moreirense F.C. in division three. He achieved promotions in 2010 and 2012, the latter signifying a return to the top tier after an absence of seven years. On 30 January 2013, after only one win in the first 16 league games of the season, Casquilha was relieved of his duties. Highlights included, however, a 3–2 home win over Sporting CP for the domestic cupafter extra time. On 6 March 2014, Casquilha signed a deal with second division side Leixões S.C. until the end of the campaign. On 30 April, however, he was suspended due to comments he made in an interview which were regarded as inappropriate and detrimental to the club's name and history. Casquilha returned to management in December 2014, taking over at U.D. Leiria in the third level. He was dismissed in March 2016, after failing with the board's aim to win promotion. Still in March 2016, Casquilha returned to the second tier with Académico de Viseu F.C. as their third manager of the campaign. In January 2017, he was hired at fellow league team C.F. União. On 26 May 2017, Casquilha moved to his former club Gil Vicente. He left on 28 December, as they were placed 15th in the standings. Halfway through 2018–19, Casquilha rejoined Leixões after the dismissal of Filipe Gouveia. After taking the team to seventh place, he left at the end of his contract for C.D. Cova da Piedade in the same league. He quit on 15 December, with the side last-placed with seven points.
