The original Clockwerk have lived over a thousand years with the intent of wiping out the Cooper Clan. Throughout the years, he would put together teams to counteract with the Coopers' skills. These teams were known as "The Fiendish Five". The recent Fiendish Five was responsible for the death of Sly Cooper's Father, and were defeated by Sly himself. Now a new Fiendish Five has been forged. An anti-Cooper Gang.
- Clockwerk II (Leader) — The duplicate of the original Clockwerk, built from his memories. He shares his hatred over Sly Cooper.
- Penelope (Machinist) — Bentley's ex-girlfriend, and creator of the new Clockwerk.
- ??? (Enforcer) — A professional silverback gorilla wrestler gone rogue.
- ??? (Mystic) — A python master of black magic.
- ??? (Demolitions Expert) — A fire ant worker. Once a miner, he uses is expertise in explosive for crimes.