This study investigated the activity, mode of inhibition, and interactions between lipoxygenase (LOX) inhibitors and compounds able to inhibit lipids oxidation (LPO) derived from green coffee beans (GCBs), wholemeal wheat flour (WF), and bread enriched with GCB, in comparison with pure chemical standards of the main active components—ferulic (FA) and chlorogenic acids (CGA). Both GCB and WF contain potentially bioaccessible and bioavailable LPO inhibitors acting synergistically. Both FA and CGA presented nearly additive interaction. Potentially bioaccessible LOX inhibitors from GCB and WF acted synergistically, whereas moderate antagonism was found for potentially bioavailable compounds. The activity of CGA and FA was quite similar (EC50 = 18.56 and 22.36 μg DW/mL, respectively) and synergistic action between these components was found. The LPO activity of functional breads was positively correlated with the percentage of GCB (R2 = 0.98). Ferulic acid and CGA acted as competitive LOX inhibitors, whereas potentially bioaccessible compounds from bread enriched with GCB demonstrated an uncompetitive mode of action. Green coffee beans, WF, and the proposed functional product could be helpful in dietary therapy and prevention of so-called lifestyle disorders related with the lipid metabolism. Moreover, this paper highlights the need to study the interactions between the active ingredients of newly designed functional products.