Moses is threatened with eviction from his hovel, unless he can come up with five crowns in three days. The next day, a play is planned at the castle. Tom, Moses and DeeDee hatch a plot to sneak into the castle and rob the guests of the play. They plan to use some of the money they steal to save Moses' Hovel. Everything goes smoothly, until the trio need to get out of the castle. All does not go to plan, and the outlaws soon find themselves on a life or death chase through the castle. Luckily, DeeDee (Lady Devereux) saves the day by taking them down a secret passage out of the castle. In the end, they manage to gain seven crowns, but Moses decides that he would prefer to live in the crypt (it is, after all, rent free).

On Sir John's orders, Captain Watt and the other guards kidnap the Blacksmith's daughter, Hope. Sir John states that unless Swiftnick gives himself up within three days, Hope will be executed. Tom devises a rescue plan in which he and Moses gain entry to the castle disguised as ladies who have just been attacked by Swiftnick. DeeDee, however, is excluded from the plan as Tom believes she is dangerous, out of control, and likely to get them into unnecessary trouble. Once Tom and Moses get into the castle, DeeDee decides to take matters into her own hands. She kidnaps Giles, Sir John's son, and plans to offer his release in return for the release of Hope. Unfortunately, Sir John could not care less if his son went missing! It is only after a backup plan goes wrong, and Swiftnick and Sir John engage in battle, that the gang manage, by chance, to rescue Hope.

When the fair arrives in town, vain Tom decides that Swiftnick should make an appearance at the fair, as a treat for what he believes to be his fans (the villagers). All does not go to plan, and when Tom makes his grand entrance the villagers wrongly think he's robbing a child. They call Sir John's guards, who go after the outlaw gang. The whole event does nothing for Swiftnick's already poor reputation. Meanwhile, 12-year-old Lord Montague arrives at the castle with his famous horse Zephyr – the fastest stallion in England. Lord Montague falls in love with Lady Devereux, and then uses Giles to get closer to her. Sir John, desperate for Zephyr, offers Lord Montague engagement with Lady Devereux in exchange for the horse. When Tom discovers that his one true love is to be ‘given' to another, he sets out at once to rescue Lady Devereux, and restore Swiftnick's tattered reputation. Unfortunately, Tom, and then Moses, fail miserably. Giles, disgruntled by the way he was used by his ‘friend

When walking through the village square a group of crazed monks mistake Moses for the ‘chosen one' and start to worship him. Meanwhile at the castle, Sir John discovers that the only portrait of Lady Devereux's parents is by a Dutch master – making it worth a fortune. Regardless of the fact that Lady Devereux has no other picture of her parents, Sir John plans to sell it. Lady Devereux, however, manages to steal the portrait and give it to Tom to look after. Sir john demands that the painting is returned, or he will burn the village to the ground. Deedee has Moses get a copy of the portrait made (as the monks will pamper to his every whim), and return this to the castle. For the plan to work, Tom plans a distraction to allow him and Deedee into the castle. He decides to use the monk's celebration of Moses, but in doing so discovers that they plan to sacrifice Moses! Luckily, the plan works, and Deedee and Swiftnick enter the castle as planned. They manage to defeat Sir John, and save M

After having yet more of his valuables stolen by Swiftnick, Sir John decides to hire the services of Captain Lucas Knife, the most notorious and bloodthirsty Thief Taker in England, to capture the gang once and for all. Scared of a premature death, Tom decides that it is time to end his career as an outlaw, and concentrate on doing well in his school work, as he promised his late mother. DeeDee sees this move as cowardice, to which Tom states that he had always planned to retire at around this time. However, Knife, bearing a grudge against the school teacher (Mr. Megson) from many year ago, frames him, and makes it appear that he is in fact Swiftnick. Tom has little choice but to resume his post and save his school teacher. Meanwhile, Captain Watt (who has been demoted to housemaid, to accommodate Knife) stumbles across a box of Sir John's jewels in Knife's chamber. When Tom arrives, Sir John mistakes him for a sidekick, but chases him and captures him anyway. At this moment, Captain W

It is Valentine's day, and Tom devises a plan to win over Lady Devereux. He will hijack a coach carrying a jewel encrusted necklace. However, all does not go to plan, and he ends up hijacking the postal coach, and stealing all the valentines! Meanwhile, Lady Devereux receives the gift of an extremely rare and exotic fruit – a banana – from Baron Pedro of Spain. In his jealousy, Sir John confiscates the gift and places it in the centre of his new creation – the chamber of doom. This room is armed with a large array of booby traps, and is almost impossible to transverse. Tom, conjuring another wild plan, buys a plum cake and laces it with a love potion from the apothecary. However, driven by his greed for food, Moses takes a bite of the cake and falls in love with Tom. When DeeDee meets the boys, she gives them a letter to Swiftnick, from Lady Devereux, that she ‘found on the Inn notice board'. In her letter, Lady Devereux asks Swiftnick to show his love for her by retrieving her stolen

It is announced that Prince Hugo will be visiting the castle. Swiftnick plans to rob the coach taking Prince Hugo to the castle, but does not want to use any of Moses' inventions, as he feels they never work. Meanwhile, Sir John wants to please Prince Hugo, as it will make him and the castle look good. Being aware that Prince Hugo is keen on torture, he instructs his inventor to build an ultimate torture machine – only problem is, Sir John drowned his inventor last week! He therefore hires Moses, and gives him a short deadline in which to build his machine, threatening to drown him as well if his invention is not ready on time, or does not work. When Prince Hugo arrives, he complains about having been stopped in the forest by Swiftnick (an attempt which obviously failed). He suggests that a good way to test the new torture machine would be to capture Swiftnick by sundown, and use it on him. At the same time, Swiftnick plans to rescue Moses, feeling that his invention is sure to malfunc

After robbing a coach, Tom realises that he has lost his lucky pants. He decides that it is not safe for him to outlaw anymore, and tells the gang that they should each find a job. Moses sees an advert for a post as a barmaid in the local public house, and decides to go for it. However, when he enters the pub, he discovers that Tom has already got the post. This infuriates Moses, who decides to try a job at the castle. When he arrives at the castle, Captain Watt refuses to give Moses a job. Moses is so desperate that, in a moment of madness, he agrees to reveal Swiftnick's true identity in exchange for a job. Tom is soon arrested and put in the dungeon. He attempts an escape, but fails as he has no confidence without his lucky pants. DeeDee manages to rescue him by disguising herself as Swifnick, to convince Sir John that he has the wrong man. Tom is released, but he does not forgive Moses. Tom refuses to do the next heist with Moses, and so goes alone. However, he has not got his luck

After discovering that Sir John has sold her Father's farmland, Lady Devereux decides to enlist the help of Swiftnick to intercept the delivery of the money gained from the sales. She writes a letter from Lady Devereux to Swiftnick, and then dresses as DeeDee to take the letter to him. After planning the heist in the crypt, Tom, Moses and DeeDee prepare to leave, but then find that the door to the crypt is jammed – there is no other way out. Believing that they will die in the lair, DeeDee decides to write about her experiences, hoping that her Father will find it in later years. There is then a flashback to what happened when they first met. DeeDee speaks of how she was held up by Tom and Moses when she first arrived at the castle. Lady Devereux pulled out a gun, and robbed both boys of their clothing. Later on, Lady Devereux decided to join the outlaw gang, so as to be able to fight against Sir John, stopping him from taking all power from her Father. She dressed as a peasant, DeeDee

Tom, Moses and DeeDee unwittingly take in Sir John's escaped feasting pig, whose milk they bottle and sell in order to raise funds to enter the annual village Box Car Race. When the sow and her piglets are recaptured by Sir John's henchmen, Tom must make a difficult choice between entering the race or saving the bacon.

Village idiot Bardolph blackmails Tom into letting him join and lead the gang after he discovers Tom's outlaw identity. Meanwhile, Sir John's bossy and demanding mother arrives in town, looking for a stupid manservant.

Tom, Moses and Deedee come across a treasure map on April Fool's Day, but realise that they will need Sir John's medallion in order to unlock the treasure. They manage to steal the necklace but leave the map in Sir John's possession, who then joins in the search for the treasure himself. How will the outlaws outfox their enemy, and is the treasure all it seems?

Deedee meets her match in Felix, the charming and handsome son of a wealthy widow, who takes a liking to her. When Moses decides to kidnap the young chap, Deedee rejects the plan, but the gang must come to Felix's rescue when Sir John's guards abduct him.