During the mid-eighteenth century, British firms were to be found trading in the Malay Peninsula, and in 1771, the British East India Company charged Captain Francis Light with the responsibility of setting up a trading post there. Light landed in the state of Penang, which was part of the Sultanate of Kedah. At this time, the Sultanate faced a number of internal and external threats, particularly from Siam, and Sultan Abdullah Mahrum Shah therefore offered Penang to Light in return for British protection. The Company, however, commanded Light to take over Penang without promising any assistance to Kedah. Light did indeed take Penang, but failed to mention to the Sultan that the British would not be providing him with any military backing until 1788, upon which the Sultan ordered the British to remove themselves from his territory. A small conflict ensued, in which the British forces razed the fort of Prai, and forced the Sultan to sign an agreement conceding their right to occupy Penang. Consequently, the Union Flag was raised for the first time in Penang on 1st May 1791.

Less than thirty years later, the British reinforced their influence in the Malay Peninsula when Sir Stamford Raffles founded modern Singapore, with the assistance of Major William Farquhar. In 1818, Farquhar had visited Tengku Hussein Shah, the son of the previous Sultan, who was in exile in Penyengat Island while his younger brother lead the Johor-Riau Sultanate. Together they drew up plans for an alliance: the British would acknowledge Tengku Hussein as the legitimate ruler of Singapore if he allowed them to establish a trading post there. Both parties signed a treaty to this effect on 6th February 1819. Hussein soon returned to Singapore, where he was installed as Sultan, but essentially remained a puppet of the British government.

Over the next century, Britain would continue to exert its influence across the Malay Peninsula, but in 1941, the Japanese launched an invasion as part of a coordinated attack that began in Pearl Harbour. Consequently, both Malaya and Singapore were under Japanese control from 1942 to 1945, until Japan's surrender at the end of the Second World War resulted in their being placed under British Military Administration. Within a year, the British administration was consolidated by the formation of the Malayan Union, from which Singapore was excluded, being considered its own crown colony.

The Union proved deeply unpopular with the local population, and by 1948, it had been replaced by the Federation of Malaya, which achieved independence from British control on 31 August 1957. Six years later, all Malayan states, as well as Singapore, Sarawak and North Borneo, formed a larger federation named Malaysia, although Singapore was expelled in 1965.

From the establishment of the Federation in 1948 to the 'October Resolutions' of 1960, the British and other Commonwealth forces were engaged in a prolonged conflict with the Communist independence fighters of the Malayan National Liberation Army. The fighting spanned the colonial period and the creation of an independent Malaya. The form of guerrilla warfare employed by the insurgent Malayan fighters, and the British responses, influenced many similar operations in the future, particularly during the Vietnam War. The conflict was never fought in Singapore, but Commonwealth forces from Australia and New Zealand used it as their base of operations.

This double-sided map of Singapore and Penang was issued by the British War Office in 1957, when the Federation of Malaya was officially formed, and while the Malayan Emergency was still being fought. The double-sided map is executed in the same style as numerous other conflict maps produced by the War Office during the mid-twentieth century: printed on fabric for durability and easy transportation, they were issued to soldiers and military personnel stationed in the region and contained not only geographical, but also political and military information as well.

The present maps were based on earlier War Office surveys of the region and updated with the political and topographic changes of the recent years. Passage through the treacherous waters of the Malacca Strait is shown with bold red lines. Relief is shown by contours and spot heights, given in metres on the Singapore map, and both metres and feet on the depiction of Penang, while depth is indicated by soundings. Beneath the maps on both sides are legends, an index and glossary, conversion tables and diagrams. On both sides, red lettering reads "RESTRICTED".