[1] This continued for centuries until the most notable interaction with Japan's invasion of Singapore during World War II.

The invasion led to a takeover of the country, after which Japan occupied Singapore for approximately four years before withdrawing following their loss in the war.

[3] Singapore has an embassy in Minato, Tokyo in addition to consulates-general in Sakai, Osaka and Nagoya.

Its maritime trade with the kingdom included Japanese products—silver, swords, fans, lacquerware, folding screens—and Chinese products—medicinal herbs, minted coins, glazed ceramics, brocades, textiles—were traded for sappanwood, rhino horn, tin, sugar, iron, ambergris, ivory and frankincense.

[6] However, most early Japanese residents of Singapore consisted largely of prostitutes, who would later become known by the collective name of "karayuki-san".

[11] Prostitutes were the vanguard of what one pair of scholars describes as the "karayuki-led economic advance into Southeast Asia".

[15] In spite of the ban, many attempted to continue their profession clandestinely; however, both the Singaporean and Japanese governments made efforts to clamp down on the trade.

However, it would recover somewhat after that, aided by devaluation of the yen and the consequent increase in competitiveness of Japanese products in Southeast Asian markets.

[23] While destroying the bridge created a slight delay, the Japanese reached Singapore on 8 February, launching into the Battle of Sarimbun Beach.

By 15 February, food and water rations were low, weapon ammunition was almost exhausted, and a final meeting was held in which Allied officers agreed that no counterattack would be possible.

[23] At 17:15, Lieutenant-General Arthur Percival surrendered to the Japanese forces, bringing an end to the seven-day battle.

Throughout this two week purge, referred to as Sook Ching, Singaporean men aged between 18 and 50 were subjected to a brief screening process and, if deemed anti-Japanese, were arrested and transported to one of several remote execution sites to be killed.

This currency was quickly subjected to major inflation, as Japanese officials would print more whenever they needed it and it was also easily counterfeited.

Singapore existed as a crown colony of the United Kingdom until 1963, during which they merged to become a state of Malaysia.

In 1980, the Singapore Government initiated a campaign to learn from Japan in terms of corporate management, labour practices and public security.

Company labour unions and koban, or neighbourhood police posts, were introduced to Singapore and became institutionalised.

[35] Japan's private sector was instrumental in the economic development of Singapore during its early years, with the Japanese corporations Seiko establishing a major manufacturing hub, and Sumitomo Chemical Corporation establishing Singapore's first-ever petrochemical plant.

[36] A major milestone in relations occurred in 2002 with the signing of the Japan-Singapore Economic Partnership Agreement (JSEPA) (Japanese: 日本シンガポール新時代経済連携協定 Nihon Shingapōru shin jidai keizai renkei kyōtei).

Both Japan and Singapore are members of the East Asia Summit, Asia-Pacific Economic Cooperation (APEC), ASEAN+3 (APT) and the World Trade Organization (WTO).

[52] The first official permanent Pokémon Center (Japanese: ポケモンセンター Pokemonsentā) outside of Japan opened in Singapore on 11 April 2019, specifically at Jewel Changi Airport.

Bee Cheng Hiang, a Singaporean company famous for its bakkwa, opened its first Japanese outlet in Ginza on 23 September 2016.

[55] In 2020, Singaporean coffeehouse chain Ya Kun Kaya Toast opened its first outlet in Shinjuku.

Many Japanese artists tend to tour Singapore due to their highly enthusiastic market for J-pop.

One of the many annual conventions featuring Japanese pop culture is Anime Festival Asia (Japanese: アニメフェスティバルアジア Anime Fesutibaru Ajia), which is held annually at Singapore's Suntec Convention and Exhibition Centre.

[62] The initial Mass Rapid Transit (MRT) network in Singapore had heavy Japanese involvement in its construction, with 11 out of 30 civil contracts in the initial MRT construction being awarded local joint ventures with the Japanese firms.

In 2013, JR East, a major railway operator in eastern Japan and Greater Tokyo, opened an office in Singapore to establish its presence in Asia for future railway projects in the region and as part of a bid for the Kuala Lumpur–Singapore high-speed rail project.

Both schools hold annual festivals open to members of the public who are interested in Japanese culture.