CREATE TABLE table_2992 ("Edition" TEXT, "Round" TEXT, "Date" TEXT, "Against" TEXT, "Surface" TEXT, "Opponent" TEXT, "Win/Lose" TEXT, "Result" TEXT)

When was the win/lose lose and the round a play-off?
SELECT "Date" FROM table_2992 WHERE "Win/Lose" = 'Lose' AND "Round" = 'Play-off'
SELECT "Date" FROM "table_2992" WHERE "Round" = 'Play-off' AND "Win/Lose" = 'Lose'