CREATE TABLE table_19429 ("School Year" TEXT, "Class A" TEXT, "Class AA" TEXT, "Class AAA" TEXT, "Class AAAA" TEXT, "Class AAAAA" TEXT)

How many times was there a class A winner when Gregory-Portland was the class AAAA?
SELECT COUNT("Class A") FROM table_19429 WHERE "Class AAAA" = 'Gregory-Portland'
SELECT COUNT("Class A") FROM "table_19429" WHERE "Class AAAA" = 'Gregory-Portland'