Mustafa Gray, 31, and 21-year-old Abdalraouf Abdallah, both of Moss Side in Greater Manchester, were charged by police investigating terrorist activity overseas.
Mr Gray says he served in the RAF under the name Stephen Gray.
The pair appeared before Westminster Magistrates' Court on Wednesday and were remanded in custody.
They were charged under the Terrorism Act after an investigation by the North West Counter Terrorism Unit.
Mr Gray is accused of intending to commit acts of terrorism, being engaged in preparation of the acts and assisting acts of terrorism. He is also accused of funding terrorism.
According to prosecutors, he bought tickets for a man - named Raymond Matimba - to assist him travelling to Syria.
He is also accused of arranging money to be transferred to another man - Abu Mutasim - for the purchase of weapons.
Mr Abdallah was charged with intending to assist others in the preparation, commission or assisting of acts of terrorism and funding terrorism.
He is accused of arranging to provide firearms to four men, including Mr Gray, and facilitating Mr Gray's travel to Syria.
He is also accused of providing Â£2,000 to a man - Mohammed Abdallah - for terrorist purposes.
Mr Abdallah had an application for bail refused by District Judge Emma Arbuthnot.
Both men were remanded in custody to appear at the Old Bailey on 19 December.
A third man arrested was released without charge.
Mr Gray previously told The Telegraph that he had served as a senior aircraftman in No 2 Squadron of the RAF Regiment.
The Ministry of Defence declined to comment on Mr Gray's military service.
A man who claims he is a Royal Air Force veteran who served in Iraq has been charged with terror offences.