Winser has her doing one round trip on the 27th May. That said I suspect a lot of the info in his book comes from Gardner as it's a official history of sorts. Plummers book says she was in the harbour on the 29th (the date is clearly wrong) and was damaged by shore fire near Calais which would suggest Route Z. Plummers book has a picture of her. Roy Martin may be able to help further.
I don't have much more. In another of his books Winser says: At 0930 on May 26 KING ORRY left for Dunkirk on transport duty but it was not until 0439 next day that she was able to enter the harbour. She embarked 1,131 men before sailing at 0803 and on passage to Dover was hit by shells from shore batteriers and subjected to air attack but reached her destination at 1100 on May 27. Roy
Hi Nick, I just copied the entry out of Winser's 'Short Sea, Long War, Cross Channet Ships Naval and Military Service in WW2'. I will send you a PM Best regards, Roy