The school was successful in creating a Borderless Learning environment in 2010 using mobile devices, WiFi & Bluetooth technology.

In 2008, the school introduced the use of mobile learning, using Bluetooth-enabled handphones to engage its lower and upper secondary students.

It was relocated again on 4 December 1999 to its current premises at 20 Jalan Damai in order to accommodate the increasing number of staff and students.

[citation needed] Due to a fall in enrolment, Bedok North was closed on 1 January 2018 and its operations merged with DMSS.

Upon accumulating a certain number of demerit points, students may be subject to disciplinary actions such as detention, caning (for boys only) or suspension.

In 1997, the principal James Ong told the Los Angeles Times that caning was administered at DMSS for offences such as fighting or disrespecting a teacher.

"[2] Designed by Samuel Teo Gek Seng, the DMSS logo incorporates the initials DSS, forming the seed of education which is of primary importance in the formative years of young people and which when carefully planted will grow into flames of faith, hope, and charity, the three components of the school motto.

[5] Students take English Language, Mathematics, Basic Mother Tongue and Computer Applications as compulsory subjects.

[5] In view of rising globalisation, Damai has realised the need for interaction with other schools all over the world, for more resources and better strategies.

Meanwhile, administrative staff accompanying the students learned about the Singapore's education system, and the mode of operation in a typical Singaporean secondary school.

As an integral part of Singapore's educational system, DMSS has planned for suitable CCA programmes to teach pupils skills, inculcate in them the correct values and desirable social attitudes, and provide for healthy recreation.

Performing groups include,[6] Guzheng,[7] Modern dance,[8] School choir (Damaivoice) [9] and Symphonic band (DamaiWindz).

[14] Uniformed Groups includes The Boy's Brigade,[15] Girl Guides,[16] NCC,[17] NPCC,[18] Scouts [19] and SJAB.

Councillors obtain LEAPS CCA points under the "Leadership" category, and are given certain rights over other ordinary students' discipline.