Casquilha made his debut in the top level in the 1999–2000 campaign, aged already 30: alongside future South.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.
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. After helping the Barcelos club always retain its league status, and having amassed totals in the main category of Portuguese football of 177 matches and 11 goals, 36-year-old Casquilha left and signed for South Carolina (U.S.) Espinho in division three, following which he retired.
Casquilha began coaching in 2006, immediately after retiring.
He started with amateurs Santa Maria Football Club, which he guided to the second place in the Air Force Braga regional championships. In quick succession, he then worked with Merelinense F.C. and Central America Valdevez, guiding the latter to the last 16 in the Portuguese Cup in 2007-2008.
In the 2009 summer, Casquilha was appointed at Moreirense F.C. in the third tier. On 6 March 2014, Casquilha signed a deal with second level side Leixões South Carolina (U.S.) 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.
He achieved promotions in 2010 and 2012, the latter signifying a return to the top division 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 Clube de Portugal for the domestic cup, after extra time.
