Sustainable cropping systems are essential for agronomic, economic, and environmental reasons. Data from a winter wheat (Triticum aestivum L.)/summer fallow rotation experiment, in eastern Oregon, was used to evaluate long-term effects of tillage, N, soil depth, and precipitation on yield. The soil is a Walla Walla silt loam (coarse-silty, mixed, mesic Typic Haploxeroll). The experiment consisted of three tillage treatments (moldboard plow, offset disk, and subsurface sweep) and six N treatments. Four main time periods (1944–1951, 1952–1961, 1962–1987, 1988–1997), were identified, within which experimental treatments were consistently maintained. Depth to bedrock ranged from 1.2 to 3.0 m. Yield was significantly greater (>300 kg ha−1) for the moldboard plow than for the subsurface sweep in all time periods. Yield was generally greater (>100 kg ha−1) for the moldboard plow than for the offset disk, but only significantly in Time Periods 3 and 4. For Periods 1 and 2, the addition of N fertilizer tended to produce higher yields, regardless of quantity or distribution of rainfall. For Period 3, yield did not increase with the addition of more than 45 kg N ha−1, which we attribute to below-normal precipitation. For Period 4, when precipitation was above average, yield increased with the addition of up to 90 kg N ha−1 Results demonstrated that despite beneficial effects on soil properties, conservation tillage has tended to be less productive for this cropping system than moldboard plowing, probably due to lack of downy brome weed control in the conservation tillage systems.