Oggy and the Tramp is the seventeenth episode of Season 5 and the 286th episode overall. It takes place in 1920s New York. It's New York 1920, and Olivia is selling flowers on the street. Joey steals them for Lady K, and has Oggy arrested instead of him. But Oggy meets Chaplin in prison and they escape, with a plan.
Oggy is tending to his rose in a vase while Olivia is selling flowers on the street. Joey appears from the awning below Oggy, suddenly and steals the rose for Lady K. Oggy attempts to chase him but was stopped by a car behind him that he was driven over. Just as Oggy has caught up with Joey, he throws the rose to the awning that distracts Oggy long enough to catch it back, and Oggy got run over by another car. Oggy catches up to Joey again but gets tied up on the wheel of an ambulance which Joey whips it to drive off. One second later, Oggy appears behind Joey but he hops onto the bicycle away from Oggy. Oggy attempts to call for a cab but to no avail. Oggy has an idea to "purposely" let a tow truck to him in order to keep up with Joey but he inserts a dynamite stick to Oggy's nose. The chase ends at the Brooklyn Bridge where Joey escapes from Oggy who gets blown up with a tire around him. Joey takes the rose to Lady K where she lives at the top of the Brooklyn Bridge, but she doesn't like it and throws it away. Oggy then meets Olivia who wonders why there is a tire around him. He then entertains her by using the tire as a hula-hoop. Joey commands Marky and Dee Dee to steal the flowers from Olivia and they do. Oggy attempts to chase after them but he doesn't know that they are on the top of the cinema entrance. The Cockroaches use a boot loaded in a Jack-in-a box to "kick" the police inspector Bob. He then turns around and stares at Oggy, thinking he is responsible for assaulting him and consequently arrests him. The Cockroaches happily flee with the flowers. Meanwhile in the jail, Oggy meets another prisoner, Chaplin, who was a joker. He asks why Oggy's in jail. A tearful Oggy reveals his story to Chaplin, and with his sharp mind and cleverness, they both escape the jail. Bob tries to chase after the escaped convicts but lose sight of them, so he continues looking. Both Chaplin and Oggy catch up to Olivia. She asked them where did the Cockroaches take her flowers to, just as Chaplin points out the flower petal from a trail of petals which the Cockroaches had carelessly left behind. Both Oggy and Chaplin follow the flower petal trail but are chased by Bob who then loses sight of them again. After successfully hides through the lamp post, Chaplin tells Oggy that he needs to buy time distracting Bob while Oggy follows the trail. Joey now brings the flowers he stole from Olivia to Lady K, and this time she becomes happy. The flower petal trails leads to the top of the Brooklyn Bridge where Oggy climbs. Marky and Dee Dee tried to stop Oggy from ruining Joey's romance with Lady K by using a fan but it is ineffective as the fan inflates air to Oggy who gets by and slaps them with their hands hanging on the edge, nearly about to fall. Oggy temporarily spares Marky and Dee Dee from falling, but eventually swats them after they get back on land. Joey and Lady K play hide and seek inside the flowers. Oggy arrives and takes back the flowers. Lady K comes to know that Joey has stolen the flowers, and as a punishment for the Cockroaches, throws them far away in the same way as the rose to the very top of the Statue of Liberty. Oggy gives the flowers to Olivia, but Bob again comes to arrest him, but at Olivia's request; explaining that Oggy did not commit any crimes, Bob leaves Oggy dropping any charges, at the same time, Chaplin drives off with Bob's police van, with Bob running before him and the Episode ends with Oggy and Olivia kissing.