Rupert and the Jolly Roger is the 53th episode of Rupert and the 1st episode of season 5.
The boys at the Rocky Bay Home for Retired Pirates need Rupert's help, when thieves make off with the treasure they've put on display for Rocky Bay's First Annual Pirate Days Festival.
- Cyril and Cubby's grandfather had a beard in Rupert and Growler. In this episode, the beard is gone
- In Rupert and the Pirates, Mr. Ribbens got a hearing aid so that he could hear better. In this episode, he doesn't use the device and it isn't mentioned either.
- In the final act of the episode where the pirates, their crew and Cyril and Cubby fight against Cyril and Cubby's grandfather, Rupert himself is missing and doesn't fight alongside them. He is onlu seen at the top on the ships crow's nest on the watch.
- The pictures that Cyril and Cubby have in their wallets and who they show to Rupert and the Pirates, are the pictures they had taken of Rupert and Constable Growler in the episode Rupert and Growler.