As a young man in college at the Briarstoke Academy, Hugo was part of the Clockwise Club, an elite group led by Alexander Truscott, but eventually quit after seeing Truscott pay two homeless men to fight each other for the club's amusement. (COMIC: The Clockwise War)
In 1989, Hugo was working in Prague with his friend Patrick Lake for MI6 investigating Yuri Azarov. He met the Eleventh Doctor, who told them of his true identity as a time traveller. Hugo took the leap of faith and believed him. When the Doctor went undercover to rescue his friends Rory and Rhoda, he ended up being kidnapped, along with Patrick's family, by Yuri. When Patrick learned of this he decided to give Azarov the book he was looking for, The Sorrows of Prague. Hugo tried to stop him, but was knocked out. The book allowed the Mavora to attempt to invade Earth, but they were stopped by the Doctor and his friends. However, the victory came with the cost of the life of Patrick's wife, Heather. Hugo later wrote about her in his personal journal. (COMIC: The Broken Man)
In the aftermath of the Cybermen's attempted invasion of Earth in 2005, Hugo and Patrick created a new division of MI6: Wonderland. With the alien technology they had amassed they were able to operate in space. They recruited Annabel, Patrick's daughter, and Danny Fisher, a promising UNIT soldier. (COMIC: The Flood, Hunters of the Burning Stone, The Blood of Azrael)
In 2013, after defeating the Prometheans, the Doctor visited the Wonderland control room and confronted Hugo. He threatened to expose Annabel's presence on Cornucopia if he did not shut the organisation down. In turn, Hugo threatened to upload data on the Doctor to every information network in the galaxy, undoing all the work he had put into erasing himself. (COMIC: Hunters of the Burning Stone)
In London, 2018, Hugo bumped into Alexander Truscott, who had just been made head of the Ministry of Defence, and therefore an overseer of Hugo's work. When questioned about the existence of Wonderland, Hugo vigorously denied its existence. When the Twelfth Doctor and Bill started working with Wonderland to uncover the mystery surrounding the Clockwise Men and Fey Truscott-Sade's change of attitude, Hugo starting doing research on his own. He eventually reported that Truscott was Fey's only surviving relative, and explained his history with him. However, Truscott got word of this, and he and the Clockwise Men ambushed Hugo in an underground London car park, leaving Hugo bound and gagged in Truscott's house for two days before the Doctor and friends rescued him.
Facing up to Truscott with the Doctor, Hugo called him insane, and was saved from being shot by Truscott by the Doctor's "cavalry" of General Kenossium and Bass Reeves, giving him chance to escape with the Doctor's group. Wilding did not join the Doctor's group in entering the Dreamspace to stop Fey Fey directly, but once the situation was resolved and peace was restored, he visited Truscott again and pointed a gun at him, stating he was relieved that Truscott would not be around any more. (COMIC: The Clockwise War)