In August 2011, after his first season with the first team of Ajax, it was decided that Castillion would go out on loan to RKC Waalwijk for the duration of the 2011–12 season. He made his debut for RKC Waalwijk on 7 August 2011, and two weeks later scored his first Eredivisie goal while playing for RKC Waalwijk. In total Castillion made 29 league appearances for the club from North Brabant, while scoring a total of six goals during league play. For the 2012–13 season, Castillion was sent out on loan a second time, this time around to Heracles Almelo, he was given the shirt number 21 coming off the bench at the start of the season, securing a starting position by November of that year. On 18 November 2012, Castillion scored his first goal for Heracles Almelo, scoring the 4th goal in a 5–1 victory at home against Roda JC Kerkrade. On 23 March 2013 Castillion extended his contract with AFC Ajax until 2014. On 17 January 2014, it was announced that Castillion was sent on loan to NEC until the end of the season.
On 25 August 2014, Castillion signed with New England Revolution of Major League Soccer. In an interview after signing, Castillion stated he hoped to "improve the level of MLS and the team". He would play approximately 14 minutes in his sole appearance in the league. On 8 December 2014, he was traded to the Colorado Rapids together with goalkeeperJoe Nasco, then released by Rapids who decided not to exercise his contract.
On 1 July 2015, he signed a four-year contract with Nemzeti Bajnokság I club Debreceni VSC.
Iceland
On 3 March 2017, he signed for Icelandic Úrvalsdeild side Víkingur Reykjavík. He signed for FH for the 2018 season. From 29 July 2018 to October 2018, he was loaned out to his former club Víkingur Reykjavík. On 19 April 2019, Castillion was loaned out again, this time to Fylkir.
Persib Bandung
On 10 February 2020, he signed for Indonesian club Persib Bandung.
International career
Castillion made his International debut in an UEFA European Under-17 Championship qualifying match for the Netherlands U-17 against Albania U-17 on 23 October 2007. The match ended in 3–0 victory for the Dutch. He played for the Dutch U-18 team on 19 November 2008 in a friendly encounter against Belgium U-18, a match which ended in 0–3 loss to the Belgians. He scored the only goal for the Netherlands U18, in his second appearance on 11 February 2009 against Luxembourg U-18, the match ended in 2–1 loss for the Dutch.
