It's possible
On september 1940, u-27 (VIIC) spotted a convoy, with 4 escorts, a light cruiser and a submarine.
The chase took 24 hours, and 200 km.
(Total manual targeting, WO only to identify ships)
27-9-40, 1822: First attack u-27 sunk a large cargo firing at a distance of more than 3000 m, fired at a small merchant as well, but the torpedo was a dud. U-27 fired over a frigate but missed; the submarine managed to escape without being detected.
28-9-40, 0100: A succesful second attack on a 7000 tons freighter.
28-9-40, 0620: The third attack was more ambicious, this time focusing on the escorts, 2 of them sunk.
28-9-40, 1621: The final attack took down the remaining 2 escorts, the cruiser and the submarine, leaving at their own luck several merchants.
Back to base, the sub crashed with the anti submarine net of Lorient taking damage.