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Zdeněk Štybar
Zdeněk Štybar won three elite cyclocross World Championships — in 2010, 2011, and 2014 — after already claiming two U-23 world titles in 2005 and 2006, giving him five combined world championships across his cyclocross career before he transitioned to road racing. On the road, Štybar won three cobbled classics — the 2015 Strade Bianche, and both Omloop Het Nieuwsblad and the E3 BinckBank Classic in 2019 — but Paris-Roubaix specifically eluded him despite repeated close calls, including a 2013 near-miss after being held up by a spectator while leading, and runner-up finishes in 2015 and 2017. His technical bike-handling skill, developed through years of navigating cyclocross's mud and off-camber turns, translated directly into the precision required on Paris-Roubaix's cobblestone sectors, even though the race's biggest prize remained just out of reach across his career. His combination of five combined elite and U-23 cyclocross world titles and his subsequent podium-level road classics career has made Štybar one of the most complete cyclocross-to-road crossover riders of his generation.
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Wout van Aert
Wout van Aert won three consecutive cyclocross World Championships — 2016 in Heusden-Zolder, 2017 in Bieles, Luxembourg, and 2018 in Valkenburg — before shifting the bulk of his focus to road racing, where he's since won ten Tour de France stages, including the green points classification in 2022. His road palmarès also includes wins at Milano-Sanremo, Strade Bianche, and the Amstel Gold Race, along with stage wins across the Giro d'Italia and Vuelta a España, a breadth of classics and grand-tour success rare for a rider who built his early reputation entirely off-road. His rivalry with fellow Belgian-Dutch star Mathieu van der Poel, carried over directly from their cyclocross duels into road racing's cobbled classics, became one of professional cycling's most closely followed individual storylines through the 2020s. His combination of three consecutive cyclocross world titles and his subsequent ten-stage Tour de France career has made van Aert one of the most complete cyclists of his generation, elite in two related but distinct disciplines.
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