2016

In June, Groenewegen won the Dutch National Road Race Championships after outsprinting Wouter Wippert.^[10] During a review of Groenewegen's Bianchi Oltre XR4 bicycle, Simon Richardson of Global Cycling Network said he is "a very easy rider to work with" in respect to the mechanics.^[11] Groenewegen won stage 4 of the Tour of Britain.^[12][13]

2017

In the Dubai Tour, which ran from late January into early February, Groenewegen came second in the general classification,^[14] having finished second in stages 1 and 2.^[15][16] Despite narrowly missing out on victory in these areas, he did win the overall youth classification.^[17] On 28 April, Groenewegen won the first stage of the Tour de Yorkshire. The stage, which was 174 kilometres (108 mi) long from Bridlington to Scarbrough, came down to a photo finish where he held off Australian sprinter Caleb Ewan.^[18] He came fourth on the second stage which finished in Harrogate.^[19] He continued this success when in May, he won two stages at the Tour of Norway.^[20][21]

The Tour de France started well for Groenewegen when he came fifth on stage 2, the first flat stage.^{[lower-alpha 1][23]} He produced two more top-10 results in the first week, with sixth in stages 6 and 7.^[24][25] After two mountain stages and a rest day in Dordogne,^[26] he returned to finish third on stage 10 – a 178 kilometres (111 mi) route from Périgueux to Bergerac.^[27][28] Groenewegen won the final stage of the race on the last stage on the Champs-Élysées in Paris.^[29][30]

2018

In February, Groenewegen competed in the Dubai Tour and won stage 1.^[31] Groenewegen held the general classification lead until the third stage when he was penalised 20 seconds after illegally drafting behind his team's car after suffering a mechanical fault. The blue jersey, given to the race leader, was lost to Elia Viviani who started the day two seconds behind Groenewegen, who dropped out of the top 10.^[32][33] He expressed his anger, saying "I had problems with my bike, the mechanicals fucked it up for me. I actually think it was a good decision by the judges but it fucked it up for me" before placing the blame on his mechanics, saying that "it's the fault of my mechanics".^[32]

In the Tour de France, Groenewegen won stage 7 after beating Fernando Gaviria and Peter Sagan, both of whom had won two stages to that point in the tour.^[34] The stage was the longest in the tour at 231 km (143.5 mi) which started in Fougères and finished in Chartres, Northern France.^[35] Groenewegen also won stage 8, beating Sagan and John Degenkolb in Amiens.^[36][37] In an interview, Groenewegen said that the sprint was "a bit messy" but he said that he "surged ahead" and took advantage of the "good opportunity".^[36]

2019

In March, Groenewegen won the first two stages of Paris–Nice. On the second stage, he found himself at the head of the race in a group of 23 riders about 30 km (18.6 mi) from the finish line, and ended up winning the stage after another split left just 7 riders contesting for the win.^[38] Later in March, he won the Three Days of Bruges–De Panne, out sprinting Gaviria and Viviani after squeezing through a gap between Gaviria and the barrier in order to open up his sprint.^[39]

Team Jumbo-Visma on their way to winning stage 2 of the Tour de France

Team Jumbo-Visma won the team time trial on stage 2 of the Tour de France, thus increasing the lead of Groenewegen's teammate, Mike Teunissen in the general classification.^[40] Groenwegen went on to win stage 7 of the Tour de France, the longest stage in the tour at 230 km (142.9 mi) finishing in Chalon-sur-Saône. He beat Caleb Ewan and Sagan, giving him his fourth Tour de France stage win.^[41][42] Groenewegen won stages 1, 3 and 5 of the Tour of Britain, beating Davide Cimolai, Mathieu van der Poel, and Matthew Walls on the respective stages.^[43][44][45]

2020

Groenewegen's 2020 season started well, with victories on stages 1 and 3 as well as the points classification of the Volta a la Comunitat Valenciana.^[46][47] Groenewegen had further success in the UAE Tour, winning stage 4 on 26 February. He beat Fernando Gaviria and Pascal Ackermann to the finish in Dubai after 173 km.^[48]

Groenewegen celebrating a win on Stage 2, 2022 Tour of Slovenia

During stage 1 of the Tour de Pologne in Katowice, Poland on 5 August, Groenewegen pushed Fabio Jakobsen into the barriers surrounding the finish line causing a very serious crash that put his rival in hospital and eventually in a medically induced coma.^[49] Groenewegen crashed as well and suffered a broken collarbone. More riders were involved in the crash; French sprinter Marc Sarreau had to abandon the race due to his injuries resulting from the crash. Groenewegen was disqualified from the race and fined CHF 500.^[50] Jakobsen's directeur sportif Patrick Lefevere said at the time that his team were considering bringing criminal charges against Groenewegen.^[51]

In November 2020, Groenewegen was handed a nine-month ban for causing the crash, backdated to the day of the incident, meaning the ban ended on 7 May 2021.^[52] The previous month, Jakobsen had to undergo facial surgery where his jaw was reconstructed and bone was transplanted. Both Groenewegen and his team Jumbo-Visma apologized and took responsibility,^[53][54] with Groenewegen saying he "deviated from [his] line" and also that he wanted to be a "fair sprinter".^[55]