The Winner’s Story
Matt Walton, of winning Team 111, speaks exclusively to Varsity
Asking Matt whether he and Matilda ever envisaged winning Jailbreak, he exclaims ‘absolutely not!’ Given the series of chance events which led to what he describes as ‘the most memorable 36 hours of our lives’, Matt and Matilda’s story almost had an entirely different ending.
‘Our original plan was to go straight to Heathrow, buy £80 flights to the nearest place with the money raised and hitchhike by road from there the next day!’
However, after fundraising around Cambridge and London and even buying £9 tube tickets to Heathrow, the pair decided to head to the Oxbridge Alumni Club at approximately 3pm. 10 metres after starting to shake their fundraising bucket en route, they met businessman Ron.
He donated £20 and the team continued walking, when 2 minutes later, Ron ran to catch up with them and offered his support.
‘He told us he was in a meeting until 6pm but to go to a travel agent until then. He asked if we could ‘maybe get flights to somewhere like South Africa, do you think you could win?’’
‘It felt like a dream when it dawned on us that the unbelievable had happened and we actually may have a chance of not just getting out of the country but actually winning!’
Whilst waiting for Ron to meet them after his interview, the pair were terrified he would not return, or would have rethought his proposal.
However, they reconvened with him 30 minutes earlier than expected to the welcome “Hey, I bet you guys thought you’d never see me again! Have a little faith!’
Not only had Ron returned but he had booked them two return flights to Singapore, a hotel for two nights and arranged for a colleague, Teo Seng Ee, to collect the pair from the airport and take them out for a meal. He even offered them spending money, which they declined.
He told them: ‘I want you guys to win. I felt like I hadn’t done anything good this week.’
After excited celebrations, the team set off to Heathrow. Now being determined to win and establishing Team 111’s destination of Hong Kong, talk turned to tactics and they decided to post onto the RAG online map only that they were heading to an “undisclosed location”, to avoid other long-haulers trying to overtake them.
Matt and Matilda, 12 hours later, were going shopping for shorts and flip-flops before retiring to the Orchard Parade Hotel. Matt recalls they just kept looking at each other and ‘shaking our heads in disbelief.’
Upon waking up at 4am for the Jailbreak results, ‘we were ecstatic.’ As champions, they then spent their day watching the sunrise by the pool, touring the city, orchard gardens and waterfront, before flying home on Monday.
Describing the experience as ‘insane’ and ‘surreal’, a dazed and still extremely excited Matt finished by saying: ‘we feel like the luckiest people ever. You hear about these things happening but you never think it’ll happen to you – two first year medics who met incidentally over the dissection table.’
Comment / Top of the slops: the competitiveness of college dining4 June 2026
News / Cambridge researchers produce ‘world-first’ AI vaccine6 June 2026
Comment / The Cambridge drift1 June 2026
Interviews / What’s the story behind Pages coffee house?8 June 2026
News / News in Brief: Cambridge crowns, council confirmations, and competitive cricket8 June 2026







