Field trials were conducted in 2010/11, 2012 and 2013 at the Royal Agricultural University’s Soil Association certified organic Harnhill Manor Farm, Gloucestershire, UK (NGR SP 075 006), to investigate suitable cultivation techniques and legume cover crops for winter and spring wheat production. Cultivation treatments included conventional tillage (CT), low residue non-inversion tillage (LRNiT) and high residue non-inversion tillage (HRNiT) as main plots while undersowing white clover (WC), black medic (BM) or no undersowing (Nus) as subplots. Wheat establishment, growth, grain yield and weeds infestation were assessed to determine the feasibility of these husbandry techniques. For winter wheat in 2010/11, LRNiT seems to be an acceptable alternative for CT. However, for spring wheat in 2012 and 2013, CT seems to be more reliable management option. The performance of undersown legumes was highly weather reliant and inconsistent in the seasons studied. Plant establishment and the succeeding yield parameters were positively related to grain yield. CT had significantly higher plant establishment than LRNiT or HRNiT in each season. For winter wheat, the competition and compensation on shoot density among CT and LRNiT did potentially outweighed cultivation-induced effects on plant establishment. This condition resulted in statistically equivalent crop growth and yields with LRNiT to that of CT. In contrast, for spring wheat in 2012 and 2013, CT that had significantly higher plant establishment also resulted in better crop growth and greater grain yields than other cultivation treatments. In all seasons, HRNiT had significantly lower plant establishment and also reduced grain yields, compared with LRNiT or CT. More soil cultivation also significantly reduced total weeds than less tilled soil such as HRNiT. On the basis of weed species, significantly higher broadleaf weeds were present under CT and significantly higher grass weeds were present under HRNiT. Out of three investigated years, legume cover crops effects were clearly observed only in 2012 with spring wheat. More vigorous growth of WC showed a significantly inverse relationship with broadleaf weeds and total weeds, compared with slow growing BM. This situation, resulted in non-significant yield components or grain yield reduction, compared with non-undersown spring wheat. In this context, white clover seems to be more suitable legume cover crop than black medic.