The aim of this study was to analyze agronomic management in the production of winter oilseed rape (WOR) in different tillage systems. The field experiment (Poland, 2016–2019) had a 35–1 fractional factorial design with two replications, where five fixed factors were tested at three levels. The experimental factors were as follows. A—tillage: (A0) strip-till, (A1) low-till, (A2) conventional tillage; B—weed control: (B0) pre-emergent, (B1) foliar, (B2) sequential; C—growth regulation: (C0) none, (C1) in fall, (C2)—in fall and spring; D—rate of spring nitrogen (N) fertilizer: (D0) 160, (D1) 200, (D2) 240 kg ha−1; E—rate of spring sulfur (S) fertilizer: (E0) 0, (E1) 40, (E2) 80 kg ha−1. Seed yields were the highest in the strip-till system (5.95 Mg ha−1). The effectiveness of weed control methods varied across different tillage systems. Foliar herbicides exerted the highest yield-forming effect in the strip-till system, pre-emergent and sequential herbicides were most effective in the low-till system, and pre-emergent herbicides were most effective in the conventional tillage system. Seed yields increased up to the N rate of 200 kg ha−1. The highest N rate of 240 kg ha−1 was justified only when S was applied in spring. Sulfur significantly increased seed yields (by 17%). The results of the study indicate that low-till and strip-till systems can be viable alternatives to the conventional tillage system in WOR production.