| 1903 | The Standard Wheel Company expands bicycle operations to include Overland Automotive. |
| 1903 | The Overland "Runabout" is introduced. |
| 1908 | John North Willys, an Overland dealer in Elmira, NY travels to Indianapolis and buys the Overland Automotive Division of Standard Wheel Company. |
| 1909 | Overland Automotive is moved to Toledo, OH. |
| 1912 | Overland Automotive is renamed Willys-Overland Motor Company. |
| 1913 | John North Willys purchases Edwards Motor Company of New York City, obtaining a license to develop Knight sleeve-valve engines. Production of the Willys-Knight automobiles begins. |
| 1914 | Willys continues increasing production and becomes the number two automaker in America, second only to Ford. |
| 1926 | The Willys Whippet debuts. Featuring a 100" wheelbase, it is the smallest car then made in America. |
| 1932 | Production of the Willys-Knight automobiles end. |
| 1935 | John North Willys, the father of the company that will later become known as Jeep, passes away. |
| 1936 | Coming out of bankruptcy following the Great Depression, the company is reorganized as Willys-Overland Motors, Inc. |
| 1940 | Two of the five Willys Quad prototype vehicles are delivered to the US Army. Powered by the 60hp "Go-Devil" engine, this vehicle has more power than the competing entries from Bantam Car Company and Ford. |