| 1949 | Dutch TT · Grand Prix | Nello Pagani | Gilera | — |
| 1950 | Dutch TT · Grand Prix | Umberto Masetti | Gilera | — |
| 1951 | Dutch TT · Grand Prix | Geoff Duke | Norton | Umberto Masetti |
| 1952 | Dutch TT · Grand Prix | Umberto Masetti | Gilera | — |
| 1953 | Dutch TT · Grand Prix | Geoff Duke | Gilera | — |
| 1954 | Dutch TT · Grand Prix | Geoff Duke | Gilera | Geoff Duke |
| 1955 | Dutch TT · Grand Prix | Geoff Duke | Gilera | — |
| 1956 | Dutch TT · Grand Prix | John Surtees | MV Agusta | — |
| 1957 | Dutch TT · Grand Prix | John Surtees | MV Agusta | — |
| 1958 | Dutch TT · Grand Prix | John Surtees | MV Agusta | John Surtees |
| 1959 | Dutch TT · Grand Prix | John Surtees | MV Agusta | John Surtees |
| 1960 | Dutch TT · Grand Prix | Remo Venturi | MV Agusta | — |
| 1961 | Dutch TT · Grand Prix | Gary Hocking | MV Agusta | — |
| 1962 | Dutch TT · Grand Prix | Mike Hailwood | MV Agusta | — |
| 1963 | Dutch TT · Grand Prix | John Hartle | Gilera | — |
| 1964 | Dutch TT · Grand Prix | Mike Hailwood | MV Agusta | — |
| 1965 | Dutch TT · Grand Prix | Mike Hailwood | MV Agusta | — |
| 1966 | Dutch TT · Grand Prix | Jim Redman | Honda | — |
| 1967 | Dutch TT · Grand Prix | Mike Hailwood | Honda | — |
| 1968 | Dutch TT · Grand Prix | Giacomo Agostini | MV Agusta | — |
| 1969 | Dutch TT · Grand Prix | Giacomo Agostini | MV Agusta | — |
| 1970 | Dutch TT · Grand Prix | Giacomo Agostini | MV Agusta | — |
| 1971 | Dutch TT · Grand Prix | Giacomo Agostini | MV Agusta | — |
| 1972 | Dutch TT · Grand Prix | Giacomo Agostini | MV Agusta | — |
| 1973 | Dutch TT · Grand Prix | Phil Read | MV Agusta | — |
| 1974 | Dutch TT · Grand Prix | Giacomo Agostini | Yamaha | — |
| 1975 | Dutch TT · Grand Prix | Barry Sheene | Suzuki | — |
| 1976 | Dutch TT · Grand Prix | Barry Sheene | Suzuki | — |
| 1977 | Dutch TT · Grand Prix | Wil Hartog | Suzuki | — |
| 1978 | Dutch TT · Grand Prix | Johnny Cecotto | Yamaha | — |
| 1979 | Dutch TT · Grand Prix | Virginio Ferrari | Suzuki | — |
| 1980 | Dutch TT · Grand Prix | Jack Middelburg | Yamaha | — |
| 1981 | Dutch TT Assen · Grand Prix | Marco Lucchinelli | Suzuki | — |
| 1982 | Dutch TT · Grand Prix | Franco Uncini | Suzuki | — |
| 1983 | Dutch TT · Grand Prix | Kenny Roberts | Yamaha | — |
| 1984 | Dutch TT · Grand Prix | Randy Mamola | Honda | — |
| 1985 | Dutch TT · Grand Prix | Randy Mamola | Honda | — |
| 1986 | Dutch TT · Grand Prix | Wayne Gardner | Honda | — |
| 1987 | Dutch TT · Grand Prix | Eddie Lawson | Yamaha | Wayne Gardner |
| 1988 | Dutch TT · Grand Prix | Wayne Gardner | Honda | — |
| 1989 | Dutch TT · Grand Prix | Wayne Rainey | Yamaha | — |
| 1990 | Dutch TT · Grand Prix | Kevin Schwantz | Suzuki | Kevin Schwantz |
| 1991 | Dutch TT · Grand Prix | Kevin Schwantz | Suzuki | Kevin Schwantz |
| 1992 | Dutch TT · Grand Prix | Àlex Crivillé | Honda | Eddie Lawson |
| 1993 | Dutch TT · Grand Prix | Kevin Schwantz | Suzuki | Mick Doohan |
| 1994 | Dutch TT · Grand Prix | Mick Doohan | Honda | Mick Doohan |
| 1995 | Dutch TT · Grand Prix | Mick Doohan | Honda | Àlex Crivillé |
| 1996 | Dutch TT · Grand Prix | Mick Doohan | Honda | Àlex Crivillé |
| 1997 | Dutch TT · Grand Prix | Mick Doohan | Honda | Mick Doohan |
| 1998 | Dutch TT · Grand Prix | Mick Doohan | Honda | Mick Doohan |
| 1999 | Dutch TT · Grand Prix | Tadayuki Okada | Honda | Tadayuki Okada |
| 2000 | Dutch TT · Grand Prix | Alex Barros | Honda | Loris Capirossi |
| 2001 | Dutch TT · Grand Prix | Max Biaggi | Yamaha | Loris Capirossi |
| 2002 | Gauloises Dutch TT · Grand Prix | Valentino Rossi | Honda | Valentino Rossi |
| 2003 | Gauloises Dutch TT · Grand Prix | Sete Gibernau | Honda | Loris Capirossi |
| 2004 | Gauloises TT Assen · Grand Prix | Valentino Rossi | Yamaha | Valentino Rossi |
| 2005 | Gauloises TT Assen · Grand Prix | Valentino Rossi | Yamaha | Valentino Rossi |
| 2006 | A-Style TT Assen · Grand Prix | Nicky Hayden | Honda | John Hopkins |
| 2007 | A-Style TT Assen · Grand Prix | Valentino Rossi | Yamaha | Chris Vermeulen |
| 2008 | A-Style TT Assen · Grand Prix | Casey Stoner | Ducati | Casey Stoner |
| 2009 | Alice TT Assen · Grand Prix | Valentino Rossi | Yamaha | Valentino Rossi |
| 2010 | TIM TT Assen · Grand Prix | Jorge Lorenzo | Yamaha | Jorge Lorenzo |
| 2011 | Iveco TT Assen · Grand Prix | Ben Spies | Yamaha | Marco Simoncelli |
| 2012 | Iveco TT Assen · Grand Prix | Casey Stoner | Honda | Casey Stoner |
| 2013 | Iveco TT Assen · Grand Prix | Valentino Rossi | Yamaha | Cal Crutchlow |
| 2014 | Iveco Daily TT Assen · Grand Prix | Marc Márquez | Honda | Aleix Espargaró |
| 2015 | Motul TT Assen · Grand Prix | Valentino Rossi | Yamaha | Valentino Rossi |
| 2016 | Motul TT Assen · Grand Prix | Jack Miller | Honda | Andrea Dovizioso |
| 2017 | Motul TT Assen · Grand Prix | Valentino Rossi | Yamaha | Johann Zarco |
| 2018 | Motul TT Assen · Grand Prix | Marc Márquez | Honda | Marc Márquez |
| 2019 | Motul TT Assen · Grand Prix | Maverick Viñales | Yamaha | Fabio Quartararo |
| 2021 | Motul TT Assen · Grand Prix | Fabio Quartararo | Yamaha | Maverick Viñales |
| 2022 | Motul TT Assen · Grand Prix | Francesco Bagnaia | Ducati | Francesco Bagnaia |
| 2023 | Motul TT Assen · Grand Prix | Francesco Bagnaia | Ducati | Marco Bezzecchi |
| 2023 | Motul TT Assen · Sprint | Marco Bezzecchi | Ducati | — |
| 2024 | Motul TT Assen · Grand Prix | Francesco Bagnaia | Ducati | Francesco Bagnaia |
| 2024 | Motul TT Assen · Sprint | Francesco Bagnaia | Ducati | — |
| 2025 | Motul Grand Prix of the Netherlands · Grand Prix | Marc Márquez | Ducati | Fabio Quartararo |
| 2025 | Motul Grand Prix of the Netherlands · Sprint | Marc Márquez | Ducati | — |
| 2026 | Tissot Grand Prix of the Netherlands · Grand Prix | Ai Ogura | Aprilia | Jorge Martín |
| 2026 | Tissot Grand Prix of the Netherlands · Sprint | Raúl Fernández | Aprilia | — |