Woodland expansion is a global phenomenon that, despite receiving substantial attention in recent years, remains poorly understood. Landscape change of this magnitude has several impacts perceived as negative on landscape processes, such as influencing fire regimes, habitat for wildlife, and hydrological processes. In southern Great Plains, Juniperus virginiana has been identified as a major contributor to woodland expansion. Adding to the perplexity of this phenomenon is its evidence on numerous landscape types on several continents, documented under varying climates. Our study aimed to quantify a direct treatment to reduce or slow down woodland expansion in an experimental rangeland in central Oklahoma, United States under three treatments: 1) herbicide, 2) fire with herbicide, and 3) control (no fire, no herbicide) within areas classified as “open grassland” in 1979. Thereafter, we identified these same areas in 2010 with remotely sensed imagery (Light Detection And Ranging) to quantify 1) total encroachment and 2) total encroachment by three size classes: a) small 1–2.5 m, b) intermediate 2.5–4.5 m and c) tall >4.5 m. Overall, of the total area classified as grassland in 1979 (277.64 ha), 31% had been encroached by 2010. Encroachment was greatest in the control treatments, followed by herbicide-only treatment application and lowest in the fire and herbicide treatment with minor differences in mean plant height (4.11 m ± 0.28). Encroached areas were mostly dominated by tall individuals (45 ± 3.5%), followed by the intermediate-height class (31.53 ± 1.10%) and the least recorded in the smallest-height class (23.46 ± 2.29%), suggesting expansion occurred during the initial phases of treatment application. The costly practice of herbicide application did not provide a feasible solution to control further woodland expansion. However, when using herbicide with fire, woodland expansion was reduced, highlighting the effectiveness of early intervention by fire in reducing encroachment. This further supports landscape-scale studies highlighting the effect of fire to reduce woodland expansion.