Junior and amateur career (2004–2008)

In 2004, the first results on the track and road for Trento-born Oss were outstanding: he excelled in the National Student Track Championships in Pordenone, collecting three podiums in the pursuit, and in the same year, he gained third place in the Madison at the European Student Championships in Fiorenzuola d'Arda.

After a year in the dark, Oss returned to the limelight in 2006 winning five races including events at Ponton [it], Isola Vicentina, Pessina Cremonese and Bibano di Godega [it]. In 2007, he won two smaller competitions while in 2008, besides three other competitions, he also participated in the World Championships in Varese, coming home in eighth place in the under-23 road race, five seconds behind the winner Fabio Duarte.^[7]

Liquigas (2009–2012)

In 2009, Oss turned professional, joining the Liquigas team;^[8] he entered the top 10 for the first time in a professional race during the Tour of Catalunya, it was in the prologue, in which he finished ninth place, four seconds detached from the winner Thor Hushovd.^[9] During the same year, he participated in the National Track Championships and came first in the team pursuit along with companions Jacopo Guarnieri, Elia Viviani and Davide Cimolai.^[10] Towards the end of the season, he was able to finish in the top five of a number of professional races: two fourth places in stages of the Tour of Missouri, and fifth in the Gran Premio Industria e Commercio di Prato.^[11]

In 2010, Oss came fifth in Gent–Wevelgem,^[12] and fourth in one of the stages of the Three Days of De Panne. He was also involved in his first ever Grand Tour when he came 124th in the Tour de France,^[13] he also won the combativity award on Stage 18, for his involvement in the breakaway. The following year, he played a key role as a lead out man for sprinter and teammate Elia Viviani in the inaugural USA Pro Cycling Challenge. It was Oss's lead-outs that secured Viviani two stage victories and the green jersey for the points classification.^[14] On Stage 6 into Denver, Viviani rewarded Oss's hard work by allowing him to win the sprint finish.^[14] In his final season with Liquigas–Cannondale, he finished third at the Gran Premio Industria e Commercio Artigianato Carnaghese,^[15] and ninth at Milan–San Remo.^[16]

Post-Liquigas (2013–2023)

Oss left Liquigas–Cannondale at the end of the 2012 season, and joined the BMC Racing Team for the 2013 season.^[2] During his five years with the team, Oss won four medals at the UCI Road World Championships in the team time trial, including gold medals in 2014 and 2015.^[17][18] He also won seven team time trials at stage races, including at Grand Tour level – at the 2015 Tour de France and the 2017 Vuelta a España.^[18][19] Individually, Oss won the mountains classification at the 2015 Tour of California and the 2017 Tour of Guangxi, and finished third at the 2013 E3 Harelbeke.

He moved to Bora–Hansgrohe for 2018,^[20] spending four years with the team – primarily being utilised as a domestique for Peter Sagan.^[21] Oss and Sagan both moved to Team TotalEnergies in 2022,^[22] with Oss winning a silver medal in the inaugural UCI Gravel World Championships held in Italy, having spent 150 kilometres (93 miles) in an attacking move with the eventual winner, Gianni Vermeersch.^[23]

Move to gravel racing

In November 2023, Oss shifted his focus to gravel cycling with the Specialized Gravel team.^[6]

Grand Tour general classification results timeline

More information Grand Tour, Giro d'Italia ...

Grand Tour	2010	2011	2012	2013	2014	2015	2016	2017	2018	2019	2020	2021	2022	2023
Giro d'Italia	—	—	—	140	103	—	111	—	—	—	—	112	—	—
Tour de France	124	100	105	—	69	97	—	—	112	89	105	115	DNF	88
Vuelta a España	—	—	—	—	—	—	—	DNF	—	—	—	—	—	—

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