Background Timor‐Leste suffered a destructive withdrawal by the Indonesian military in 1999, leaving only 20 Timorese‐based doctors and no practising specialists for a population of 700 000 that has now grown to 1.2 million. Methods This article assesses the outcomes and impact of Royal Australasian College of Surgeons (RACS) specialist medical support from 2001 to 2015. Three programmes were designed collaboratively with the Timor‐Leste Ministry of Health and Australian Aid. The RACS team began to provide 24/7 resident surgical and anaesthesia services in the capital, Dili, from July 2001. The arrival of the Chinese and Cuban Medical Teams provided a medical workforce, and the Cubans initiated undergraduate medical training for about 1000 nationals both in Cuba and in Timor‐Leste, whilst RACS focused on specialist medical training. Results Australian Aid provided AUD$20 million through three continuous programmes over 15 years. In the first 10 years over 10 000 operations were performed. Initially only 10% of operations were done by trainees but this reached 77% by 2010. Twenty‐one nurse anaesthetists were trained in‐country, sufficient to cover the needs of each hospital. Seven Timorese doctors gained specialist qualifications (five surgery, one ophthalmology and one anaesthesia) from regional medical schools in Papua New Guinea, Fiji, Indonesia and Malaysia. They introduced local specialist and family medicine diploma programmes for the Cuban graduates. Conclusions Timor‐Leste has developed increasing levels of surgical and anaesthetic self‐sufficiency through multi‐level collaboration between the Ministry of Health, Universidade Nacional de Timor Lorosa'e, and sustained, consistent support from external donors including Australian Aid, Cuba and RACS.