Since Singapore left Malaysia to become an independent country some forty years ago, bilateral relations between the two neighbours, bound by centuries of historical and economic ties, have undergone many stages of ups and downs. The period stretching from 1997 to 2002 under the Mahathir administration was by far the most stressful in the short history of relations between Singapore and Malaysia, with a number of issues reaching confrontational level and thus rendering them more difficult to resolve. Many old questions were resurrected, such as the return of Central Provident Funds (CPF) contributions to West Malaysian workers previously employed in Singapore, railway land and the Tanjong Pagar railway station, pricing of water supplies from Malaysia to Singapore, Singapore airforce access to Malaysian airspace, a new bridge to replace the existing Causeway, the Pedra Branca dispute and land reclamation by Singapore near the Malaysian border.

The failure to resolve the issues despite many rounds of negotiations has caused some confusion and concern among governments and the general public about the bitter exchanges between the top officials of both countries. Foreign investors began to question the wisdom of investing in an area that appeared increasingly volatile. What was of greater concern was that the acrimony had generated unhealthy trends emerging at the people-to-people level. For example, the Singapore contingent to the Southeast Asia (SEA) Games in Kuala Lumpur in 2001 was booed during the march-past. Taking the cue from the leadership, officials began to curtail all sorts of contacts, including the Civil Services and Foreign Ministries games. Among the few that survived was the annual University of Malaya-National University of Singapore (UM-NUS) golf tournament, due in part to the UM Chancellor Sultan Azlan Shah, the true statesman that he is, insisting that the tournament must not be held hostage to the vagaries of political fortune. With the level of acrimonious exchanges growing day by day and the realization that the resolution of the issues of contention would not be forthcoming as long as Mahathir remained in office, Singapore decided to sit things out.