After four riders went clear with 50 kilometres to go, Bennett was dropped by the chasing group on the penultimate climb. However, as riders who were up the road cracked, Bennett slowly churned by them, measuring his effort and passing many of the contenders for overall victory, including teammate Primoz Roglic, Michael Woods, Egan Bernal and world champion Alejandro Valverde.
Roglic and Bernal were part of the quartet leading the way, but were dropped by Pinot and Vincenzo Nibali, who went toe to toe until the top of the penultimate climb, when eventually Pinot's persistent attacks paid off, dropping Nibali and riding away solo for the biggest win of his career.
Nibali got caught by the chasing pack, but found enough energy to attack again with two kilometres to go, and finished second, 32 seconds behind, before Dylan Teuns led home a small group of riders for third.
The best of the rest was Bennett, who crossed the line by himself to finish his season on a strong note.
Best finish by a New Zealander rider in the five monuments:
Il Lombardia - 10th (George Bennett, 2018)
Paris Roubaix - 10th (Hayden Roulston, 2010)
Milano Sanremo - 15th (Eric McKenzie, 1984)
Ronde Van Vlaanderen - 21st (Hayden Roulston, 2010)
Liege-Bastogne-Liege - 52nd (Christopher Jenner, 1999)