I don't know the details of all of his escapes, but I think he must have been sort of like Steve McQueen in The Great Escape in that he probably spent half his time in the 'cooler' for escaping.
The first one was after he'd parachuted out and evaded the soldiers who were hunting him. He got to within a few km of the Swiss border but had to take refuge in a chalet from a blizzard, and when the storm lifted, the Wermacht were tracking him with dogs. He was then taken to Gestapo interrogation in Frankfurt.
I think the 2nd or 3rd time was when the train he was on was attacked by allied aircraft and he managed to get out and into a field in Poland that was being worked by non-commissioned prisoners. He tried to get a British sgt to trade uniforms but the sgt refused, as he thought that he had it pretty safe to sit out the war and lots of food since he worked the farm for the Germans. so Dad was recaptured not more than a mile away from the train.
When he was captured after the 5th attempt, the kommandant threatened him with execution if he escaped again. So the 6th time he found himself in front of a firing squad where they airmed, but never got the order to fire. I had a photo of that.
The 7th time perhaps wasn't quite an escape, since on April 21, 1945 (this was after the Long March from Stalag Luft III), he was at Stalag XI B, and in the morning when he woke up, all the Germans were gone, they'd deserted the camp. Dad went to the library and 'checked out' a book, "Mein Kampf" (it has a stamp of Hitler's autograph in it) with the camp number stamped in it and Dad dated it, that's how I know when and where. He then had to cross the front lines of the Russians to get to the American side and freedom. He got through and across the river and was repatriated the day U-711 was sunk.
I doubt if any of his escapes were big important ones, but the way Dad told it, the main idea was not necessarily to get home (Although that was a nice bonus if you did). The big idea was that when you escaped, it took hundreds of soldiers to search for you, soldiers who might otherwise be at the front and able to helop their war effort. So the longer you could stay on the run, the more it weakened the enemy.