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The Three Mile Handicap takes place on the last Tuesday of each month from April to August. It is a roughly three mile time trial on Wimbledon Common, for members only.
For full results go to the results database (link on home page)
Wimbledon Windmilers 3 Mile Handicap Winners
| Year | Winner | Runner Up | Third | Participants |
| 2023 | David Shute | Jeremy Copp | Martin Jimack | 115 |
| 2022 | Claire Morgan | Charlotte Rutherford | Giorgio Santini | 117 |
| 2021 | Stephanie Langton | Anne Davies | Michaela Williams-Black | 98 |
| 2020 | Not Run | Not Run | Not Run | |
| 2019 | James Spinks | Richard Weiss | Andrew Alcock | 148 |
| 2018 | David Shute | John Gorst | Ella Waddingham | 145 |
| 2017 | David Turner | Ella Waddingham | Phil McElhinney | 145 |
| 2016 | Julie Burgess | Nick McKay | Polina Stucke | 121 |
| 2015 | Ricky Wood | Andy Allan | Denise Barnett & Gavin Mclaughlan | 153 |
| 2014 | Neil Guthrie | Phil McElhinney | – | 168 |
| 2013 | Keith Lines | Neil Guthrie | Nick Mckay | 223 |
| 2012 | Jonathan Barnett | Barbara Gloor | Peter Archer | 189 |
| 2011 | John Carter | Derek Gilby | Beverly Walker | 214 |
| 2010 | Alison Russell | Daniel Doy | Denise Winter | 254 |
| 2009 | Toni Riding | Michael Daniels | Jonathan Barnett | 216 |
| 2008 | Lorna Young |