Gesink also won the Giro dell'Emilia twice and offered some good performances on Grand Tours and one-week stage races, thanks in part to his climbing and time trialing abilities.

At the Junior World Championships of 2004 UCI Road World Championships in Verona, Gesink finished eighth in the individual time trial and sixth in the road race, while riding for team De Peddelaars in Aalten.

He finished third overall in Volta ao Algarve and won the overall classification and the third stage of Settimana Ciclistica Lombarda.

He later won a stage and the overall classification of the Circuito Montañés and finished second in the prestigious Tour de l'Avenir.

[8] In his first year as professional cyclist, Gesink won the young riders jersey in the Tour of California.

In his 2nd year as professional, in 2008, he showed progression by winning the hardest stage in the Tour of California, where Gesink rode away on the final climb, with only Levi Leipheimer holding his wheel.

They stayed ahead on the final 35 kilometres (22 miles) of downhill and flat and Leipheimer did not contest Gesink in the sprint.

Afterwards Gesink focused on regaining his form for the World Championships in Mendrisio, but he had not recovered fast enough and finished off the pace.

However, a week later he was back to his old self and took the victory in the Giro dell'Emilia, beating Jakob Fuglsang and Thomas Löfkvist to the line in an uphill sprint.

Due to the absence of, among others, Alberto Contador and Cadel Evans, he started as one of the favorites for the Tour of the Basque Country.

In the closing time trial he had a bad day and lost his leading position to Fränk Schleck, and finally finished fifth.

In September he suffered a crash in training where he broke his leg in four places, and had a surgical operation which left screws and pins in his body.

For the Tour de France, he was considered one of the Dutch hopefuls who might finish in the top ten, but he fell in the massive crash that occurred on the sixth stage, damaging his ribs.

[14] He then went on to participate in the Vuelta a España, and he made an impact by finishing in sixth position overall behind the winner Alberto Contador (Saxo Bank–Tinkoff Bank).

His season however was disrupted by heart problems for which he received surgery, preventing him from riding the Tour de France, switching his hopes to the Vuelta a España.

One week after the Tour Down Under, he rode the Cadel Evans Great Ocean Road Race and finished 11th as he did in 2017.

[20] His first race leader's jersey since 2012, Gesink ultimately ceded the lead to teammate Mike Teunissen at the end of the following stage.