About Predict the Ride
Predict the Ride is a skill-based prediction competition that brings together charitable fundraising and the excitement of endurance sport. Participants choose an entry package, predict how long it will take a cyclist to complete a designated route, and the supporter whose prediction comes closest to the official finish time without going over wins a prize. Every entry directly supports a registered charity, creating an engaging way to raise money for important causes through a game of skill.
The platform is designed for cycling enthusiasts, sports fans, and anyone who wants to support charitable organisations in a fun and interactive way. Unlike a lottery or raffle, the winner is determined by the accuracy of their prediction — rewarding knowledge, strategy, and careful calculation rather than luck. Each prediction slot can only be chosen once, adding an element of strategy to every entry.
Who builds it
Predict the Ride is built by Play Fund Win
Play Fund Win is a platform dedicated to creating engaging fundraising experiences that bring communities together around sport and charity. It runs prize draws, 50/50 draws and prediction competitions for clubs, charities and foundations, and it handles the payments, the entries and the compliance so an organiser does not have to.
Predict the Ride is the Prediction Challenge format, and the same format works for any timed effort — a ride, a run, a swim, a marathon, a 24-hour challenge. If you would like to run one for your own cause, the Run your own page explains how it works and what it costs.
Who is behind it
Meet the co-founders
Dean Lynn
Co-Founder & CEO
Dean built Play Fund Win from the ground up, and still works directly with the clubs and charities using it to decide what gets built next. He started it because too many fundraising platforms take a punishing cut of money raised for a cause — he takes the view that a 30% platform cut is simply theft, and that the technology should be invisible to the people doing the fundraising. The platform now runs draws and competitions for Premier League club foundations, national charities and grassroots clubs across the UK.
Dean on LinkedIn (opens in a new tab)
Steve Lightfoot
Co-Founder & CRO
Steve leads the commercial side of Play Fund Win, drawing on years of experience across sport, fundraising and partnerships. He works with club foundations, elite clubs and live event partners to get campaigns like Predict the Ride in front of the supporters who will back them.
Steve on LinkedIn (opens in a new tab)Questions for the team? Email hello@playfundwin.com or follow Play Fund Win on LinkedIn.
The cause
The first campaign supported Friends of The Oaks, a Moray-based charity that provides financial support to The Oaks Palliative Care Unit in Elgin. All money raised stays in the local community and funds equipment, complementary therapies, and comfort items for patients and their families.
David cycled 90 miles from Elgin to Dornoch on 14 August 2026. Supporters predicted his finish time, every slot on the board was taken, and the campaign raised £2,020 from 80 supporters. Entries are closed and the winning prediction has been announced.