Mohammed Saboor, 25, from High Wycombe, was found guilty of planning to send a pair of protective ballistic glasses to Omar Hussain in December 2013.
He was jailed for 21 months.
The Old Bailey jury was not told about Hussain's interview, where he said the only reason he would return to the UK is "if I wanna go plant a bomb".
During the trial, jurors heard Saboor, a BMW worker and a father of two, escorted Mr Hussain to Gatwick Airport, where his friend told police that he was travelling to Turkey to do aid work.
Once Mr Hussain was in the country, the pair, who maintained contact through WhatsApp messages and phone, began discussing the purchase of ballistic glasses.
Prosecutor Alison Morgan said: "These glasses are clearly of use to someone engaged in warfare, protecting the wearer from shrapnel injuries to the eyes."
Saboor accepted he was aware Hussain was associated with armed groups opposed to Syrian president Bashar Assad's regime.
He had denied the charge of entering into an arrangement to make property available to another, knowing it might be used for purposes of terrorism.
Hussain's interview was broadcast last August, in which he was identified as Awlaki, in reference to dead al-Qaeda cleric Anwar Al-Awlaki.
He told a journalist he was fighting for the return of the "Caliphate" and laughed when he confirmed that Islamic State had beheaded three or four people, displaying their heads in the town centre.
He also professed a hatred for the UK
Sentencing, Judge Peter Rook QC said: "I take into account that this was January 2014 so it was significantly before some of the worst excesses of Isis became generally known.
"Nevertheless, it is quite clear that you entered into this arrangement knowing that the item was to be used for terrorist activities on the battlefield."
A man who attempted to help a British jihadist in Syria who laughed about Islamic State beheadings in a BBC Newsnight interview has been jailed.