In pictures: Old Town restaurant is destroyed as 100 firefighters tackle blazes
Click here to view images of the fire.
Crews spent hours tackling two major fires in old and complex buildings in the city centre as onlookers watched flames that shot into the air.
At one point, firefighters had to retreat from a blaze, creating a waterfall of water to halt it spreading.
The first incident started at 8:07pm when a fire broke out in Khushi's Indian Restaurant in Victoria Street.
There were no injuries at the restaurant as diners were able to evacuate once alerted by smoke detectors.
Crowds gathered at a vantage points off the Royal Mile to watch as seven appliances and more than 45 firefighters battled to control a blaze.
Silhouetted against the flames, a firefighter 100ft up a turntable ladder directed a hose at the flames shooting out of the former church.
Two neighbouring bars. Finnegan's Wake and the Liquid Room. were evacuated, Lothian and Borders Fire and Rescue Service said.
High winds meant that no sooner had one section been extinguished but another seemed to catch fire, with bursts of sparks billowing up on to the roofs of adjacent buildings.
Brain Dodds, 21, an IT student from Falkirk, said police had prevented him going down Victoria Street. He said: "The flames were really high and people in the building next door were hanging out their windows wondering what was going on. It was quite scary wondering if there would be a gas explosion.
"We went up the Royal Mile and were standing on the balcony above Victoria Street but the police moved us on."
The fire service said the building was very complex and had been renovated and changed over the years, creating "undetected fire spread" with new pockets of flames erupting out of control.
A spokeswoman added: "At one point we had to withdraw our firefighters and created a waterfall of water in a stairwell to prevent further spread. The fire was brought under control but the roof collapsed. The location also added to the complexity of the fire and it was hard to get appliances up there."
At 9:04pm, Rick's Bar in Frederick Street was evacuated after smoke was detected from an adjacent cellar. It spread into flats above the bar and seven residents had to be led to safety. Nobody was injured. Five appliances and 30 firefighters were in attendance and the incident was under control by 11:11pm.
At 9.24pm, a chip-pan fire set a flat alight in Moredun Park Street where two appliances attended. One woman was treated by ambulance staff for smoke inhalation, the only injury in the three blazes.
Brian Allaway, chief fire officer, said: "(It] was a difficult night for the fire and rescue service with two major incidents in the centre of Edinburgh, while dealing with a number of others.
LAST night's fire brought back memories of the Cowgate blaze on Saturday, 7 December, 2002 which destroyed 11 buildings.
The fire started just after 8pm and took three days to bring under control. It was described at the time as the worst in living memory and caused millions of pounds' worth of damage to grade A-listed buildings. Nobody was injured, but 150 people were evacuated from their homes.