Riding Against both Father and Son

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Wasn't there like a five year gap between their careers? Tons of riders have ridden against both (not many on the same team, though, of course).
Greipel started with T-mobile in 2006, whereas E. Zabel rode with T-mobile team up until the end of 2005. He then moved to Milram until 2008. They against each other in a few Deutschland Tours and a couple of grand tours as well. Then R. Zabel is on ISN with Greipel and rode in various sprints against him when they were at Katusha and Lotto respectively.
 
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This is in the Road race section of the forum, but the OP didn't specify, so there will be a large number of Cyclocrossers whose career is current and of at least 5 years duration who will have competed against both Sven and Thibau Nys. That is a much shorter intergenerational gap than is probably typical.
 
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Lots of father/ sons duos who are unlikely to have had people race against both, Jean Francois/Julien Bernard, Jean Rene/Giovanni Bernaudeau, Jean Claude/Yoann Bagot, Dietrich/Bjorn Thurau, Patrick/Antwan Tolhoek, Milan/Matej Jurco, Luciano/Matteo Rabottini, Lucien/Laurent Didier, Giovanni Fidanza has 2 daughters that have been pro.

Scary thing is I remember quite a few of the Fathers racing.

Edit: Rebellin might have raced against a few of those father/son combos. I am sure that Rebellin has raced against the late Franco and son Davide Ballerini
 
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Giovanni Fidanza has 2 daughters that have been pro.
If we're including these then we can add Frank & Cameron Vandenbroucke; Gerrie & Roxane Knetemann; Magnus and Elynor Bäckstedt; Sergey Sukhoruchenkov and Olga Zabelinskaya; Servais and Britt Knaven; perhaps we might be able to find some who've raced against mother and daughter as well, as Lea Lin Teutenberg is the daughter of Lars and Ina-Yoko Teutenberg. Ina retired in 2013 and Lea turned pro in 2018 and is riding for a pretty solid team in WNT.

Lisa Brennauer was a teammate of Ina at Specialized-Lululemon in 2012-13 and has been a teammate of Lea at WNT since 2019.
 
I think he only rode against Adrie VDP on the road, but Sven Nys did cross against Adrie, Mathieu and David.

David Dekker might have raced against some guys Erik Dekker raced against already. If not he certainly will this year.
Valverde will meet David Dekker next week in the UAE Tour for the first time. He had lots of races against Erik Dekker but no direct battles for victories.
 
If we're including these then we can add Frank & Cameron Vandenbroucke; Gerrie & Roxane Knetemann; Magnus and Elynor Bäckstedt; Sergey Sukhoruchenkov and Olga Zabelinskaya; Servais and Britt Knaven; perhaps we might be able to find some who've raced against mother and daughter as well, as Lea Lin Teutenberg is the daughter of Lars and Ina-Yoko Teutenberg. Ina retired in 2013 and Lea turned pro in 2018 and is riding for a pretty solid team in WNT.

Lisa Brennauer was a teammate of Ina at Specialized-Lululemon in 2012-13 and has been a teammate of Lea at WNT since 2019.
You could possibly also find someone, who has raced against both Elynor Bäckstedt and Megan Hughes, although there was a bit of a gap between their careers.

Edit: Trixi Worrack has done that even before she became teammates with Elynor. If they didn't compete earlier both Worrack and Hughes did the 2000 Liberty Classic. And Worrack and Bäckstedt "met" during the 2019 Tour de Yorkshire. Worrack got beaten on both occasions.
 
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Valverde will meet David Dekker next week in the UAE Tour for the first time. He had lots of races against Erik Dekker but no direct battles for victories.
I can spot ten riders at UAE Tour that according to PCS raced against Erik Dekker. Might be more.

Examples:
Valverde: Tour de France '05
Richeze: Milan-Sanremo '06
Iljo Keisse: Ster Elektrotoer '06
Luis Leon Sanchez: Paris Nice '06, Milan-Sanremo '06
Sabatini: Ster Elektrotoer '06
Ladagnous: Criterium International '06
Greipel: Gent-Wevelgem '06
Nibali: Paris-Nice '06
Pozzovivo: Milan-Sanremo '05
Bonnet: Tour du Picarde '04

I suspect at one point or another this year Philippe Gilbert and others will add to the list of riders having done the double-Dekker(sorry, not sorry).
 
Since we've been discussing this topic, interesting article in Marca. We have this about the 3 sets of father and son pairings he's raced against (not just racing at the same time, but actually raced in the same races as).
The 3 sets are:
Erik and Rick Zabel, Nicola and Riccardo Minali, and Erik and David Dekker


 
That's not a complete list, though - more like lazy journalism. Valverde also raced against both Farazijn father and son. Against Peter Farazijn e.g. at Milan-Sanremo 2002, against Maxime Farazijn at Flèche Wallonne 2017.

Even more curious: he raced agains both father and son Giannetti at the same race. Against Mauro Giannetti at the 2002 Tour de Romandie and against Noé Giannetti at the 2010 Tour de Romandie.
 
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That's not a complete list, though - more like lazy journalism. Valverde also raced against both Farazijn father and son. Against Peter Farazijn e.g. at Milan-Sanremo 2002, against Maxime Farazijn at Flèche Wallonne 2017.

Even more curious: he raced agains both father and son Giannetti at the same race. Against Mauro Giannetti at the 2002 Tour de Romandie and against Noé Giannetti at the 2010 Tour de Romandie.
Add another father-son duo Valverde has raced against.

Ivan Quaranta (Vuelta 2002) and Samuel Quaranta (GP Industria & Artigianato 2021).
 
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Beryl and Denise Burton were racing against each other for several years, so there will be a whole load of riders who raced mother and daughter in the same race, most notably the British Nationals in 1973 & 1975 (Beryl won) and 1976 (Denise won)
 
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