In May 2018, he was named in the startlist for the 2018 Giro d'Italia.[6] He was in 12th place on the general classification at the start of stage 19 but crashed during the stage breaking his collarbone. He then withdrew from the race.[7]
O'Connor started the 2020 Giro d'Italia. He achieved his first Grand Tour stage win on stage 17 after finishing second on stage 16 the day before.[9][7]
In October 2020, O'Connor signed a contract to join the AG2R Citroën Team for the 2021 season.[10]
O'Connor won stage nine of the 2021 Tour de France after getting in the breakaway and then riding solo for the last seventeen kilometres of the mountain stage. His victory elevated him to second in the general classification at the end of the stage.[11] He finished the Tour in fourth place overall.[12]
In 2024, O’Connor won stage six of that year’s edition of the Vuelta a España after going on a solo breakaway. His victory gave him a stage win in all three grand tours, and the opportunity to wear the red jersey as he took over a four-minute lead over the rest of the peloton. He wore the red jersey until stage 19 of the race, when he lost the lead to 3-time champion Primoz Roglic, but defended his second place in the podium until the end of the competition for his best ever result in a Grand Tour.[13]
O'Connor came second in the 2024 UCI World Championship.[14]
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