The mission involved taking out a ground target in enemy territory, while fending off adversarial air forces and threats on the ground.
Republic of Singapore Air Force (RSAF) weapons systems officer Chia Chi Yu, 32, planned and led a multinational team in the simulated scenario in a two-week exercise in Nevada, in the United States.
The exercise involved some of the most advanced fighter jets in the world, such as the US Air Force's (USAF) F-22s and Royal Saudi Air Force's Eurofighter Typhoons.
The Singaporean was recognised as the top performer out of 19 mission commanders - he was named the Overall Outstanding Mission Commander at this year's Exercise Red Flag - Nellis, hosted by the USAF from Aug 14 to last Friday.
Captain Chia is from the RSAF's Peace Carvin V Detachment, based in Mountain Home Air Force Base, Idaho.
The Singapore team was also recognised as the Outstanding Aircraft Maintenance Unit at the exercise at Nellis Air Force Base. The Singapore detachment deployed eight F-15SG fighter aircraft and more than 100 personnel.
About 70 aircraft from Saudi Arabia, Singapore and the US were involved, with observers from Chile, Romania and Oman.
As a weapons systems officer, Capt Chia typically sits behind and works with the pilot to control the aircraft's weapon systems and navigate the flight. He said as a mission commander, he had to make decisions under pressure.
70 Number of aircraft from Saudi Arabia, Singapore and the US involved in the exercise
He added: "The award... is definitely a recognition and testament to our training standards, benchmarked with the rest of the participants in this exercise."
The Outstanding Aircraft Maintenance Unit award was presented to the RSAF ground crew for their efforts in ensuring that the F-15SGs were in tip-top condition throughout the entire exercise.
Detachment commander Lieutenant-Colonel Oon Kok Choon said: "The exercise provided a realistic training environment for both our air and ground crew, and I am proud that our RSAF team upheld the high standards and continued to perform well."
The RSAF, which has been taking part in the exercise since 1982, won three awards in 2015. Participants typically engage in air combat and strike missions to sharpen operational competencies.