Restoring highly degraded sites in Oregon’s Willamette Valley to diverse native prairie plant communities is an important component of regional conservation strategies. However, creating or reassembling desired native plant communities is a tremendous challenge for restoration practitioners, and useful practical approaches are needed. Here, we describe an implementation strategy we developed for restoring intensively managed agricultural sites to native wet prairie that integrates relevant scientific research and lessons learned from previous restoration experience, with a particular focus on sequencing disturbance, colonization, and competitive actions to achieve desired outcomes. Then, we report vegetation monitoring results from four projects where we used this implementation strategy to assess if progress is being made to achieve our two a priori project objectives: (1) establishing a plant community with 50 or more native plant species, and (2) establishing a plant community with > 70% absolute cover of native plant species. By the second growing season after seeding, all four projects had more than 40 native species and native cover exceeded 90%. For the two projects for which we have data during the fifth growing season, native species richness exceeded 50 and absolute native cover exceeded 100%. Furthermore, percent cover of native annuals decreased and percent cover of native perennials increased by the fifth growing season, consistent with predictions from succession. These results indicate that our implementation strategy can assist the efforts of landowners and managers to restore high diversity prairie communities from highly disturbed agricultural sites.