New Zealand has been a second home to a significant number of Royalists, alumni of the prestigious Royal College, Colombo. For decades, these individuals, bound by their shared experiences and values, sought opportunities to reunite and celebrate their connection to their alma mater. In 1990, this desire culminated in a momentous initiative led by a group of passionate Royalists, Mahe Weerasinghe, Lal Senaratne, Dr Nagalingam Rasalingam and Dr Stanley Wijeyaratne, Their vision sparked the beginning of what would become a highly anticipated tradition—the annual Royal College Old Boys Dinner Dance.

Held in Auckland, this gathering quickly became a symbol of unity for the Royalist community in New Zealand. Under the informal banner of the Royal College Old Boys Association of New Zealand, the dinner dance provided alumni the opportunity to reconnect with old friends, reminisce about their school days, and celebrate their shared legacy. For three consecutive years, from 1990 to 1992, the event continued to grow in popularity, becoming a fixture in the social calendar for Royalists across the country.

In 1993, the responsibility of organising the event passed to Dr Nilkanth de Zoysa, who was then working at the Whanganui Hospital and Dr Nihal Gonsalkorale of Wellington who hosted the events in their respective cities. Despite the change in leadership and locations, the annual dinner dance maintained its allure, with Royalists from all over New Zealand eagerly anticipating the gathering each year. Though the dinner dance was primarily for Royalists, it attracted a wider audience including alumni from other schools as well as establishing itself as one of the most prominent social events in the Sri Lankan expatriate community.

The Royal College Old Boys Dinner Dance continued to be a much-loved event alternating between Auckland, Wanganui, and Wellington until it came to an unexpected halt in 1996. The gathering had brought joy, unity, and a sense of belonging to Royalists living far from home. Although the tradition ceased, its significance endured in the hearts of those who had attended, with many hoping that the event would one day make a return.

In 2014, two Royalist batchmates from the Group of 2000, Chamira Ranatunga and Robbie Peris, envisioned a new event in Auckland. Initially, they planned a dinner dance to be hosted aboard a boat on the Waitemata Harbour. However, after looking at all other options, they pivoted towards organising a cricket match, creating a new tradition: the NZ Royal-Thomian Cricket Encounter.

The inaugural match occurred on March 23, 2014, at the Mellons Bay Primary School Ground. Bhagya Wijeratne captained the Royal College team and Deshan De Alwis captained the S. Thomas' College team. Royal emerged victorious winning by 9 wickets. This game was filled with excitement, with standout performances such as Robbie Peris taking an astonishing 5 wickets for just 6 runs, and Kasun Eranga scoring a rapid 52 runs. Since then, the Royal-Thomian Cricket Encounter has become a much looked forward to annual event to strengthen the alumni bond and inspire the creation of similar inter-school competitions fostering an enduring rivalry and friendship.