Starting once again on Westminster Bridge in London, 88 racers lined up for the Transcontinental Race No. 2 in 2014. Kristoff Allegart, winner of TCR No. 1, quickly took the lead followed closely by Josh Ibbett, a fresh face on the bikepacking race scene. Control Point 1 was at the iconic Café Reveil au Matin in Paris, the start of the first Tour De France in 1903. Passo Stelvio had proven challenging enough in TCR No 1 to merit a revisit as CP 2 for a second year running. The addition of a third Control Point sent riders up the spectacular Lovcen or “Black Mountain” for which Montenegro got its name. The race finished in Rumeli Hisari, an Ottoman Fortress on the European shore of the Bosphorus Strait in Istanbul. Allegart finished in 7 days, 23 hours and the 1st female prize was awarded to Pippa Handley in 12 days, 4 hours.

This was the first race to feature the now iconic and much copied numbered caps. Mike and Anna began hand printing the caps with vintage letterpress blocks that are still used today.