Almonds have gained consumers’ attention due to their health benefits (they are rich in bioactive compounds) and sensory properties. Nevertheless, information about phytoprostanes (PhytoPs) and phytofurans (PhytoFs) (new plant markers of oxidative stress and compounds with biological properties for human health) in almonds under deficit irrigation is scarce or does not exist. These compounds are plant oxylipins synthesized by the oxidation of α-linolenic acid (ALA). Besides, they are biomarkers of plant oxidative degradation and biologically active molecules involved in several plant defense mechanisms. hydroSOStainable or hydroSOS mean plant foods made from from plants under controlled water stress. Almonds are a good source of polyunsaturated fatty (PUFAs) acids, including a high content of ALA. This paper aimed to describe the influence of diverse irrigation treatments on in vitro anti-oxidant activity (AAc) and total phenolic content (TPC), as well as on the level of ALA, PhytoP, and PhytoF in “Vairo” almonds. The AAc and TPC were not affected by the irrigation strategy, while the in vivo oxidative stress makers, PhytoPs and PhytoFs, exhibited significant differences in response to water shortage. The total PhytoP and PhytoF contents ranged from 4551 to 8151 ng/100 g dry weight (dw) and from 33 to 56 ng/100 g dw, respectively. The PhytoP and PhytoF profiles identified in almonds showed significant differences among treatments. Individual PhytoPs and PhytoFs were present above the limit of detection only in almonds obtained from trees maintained under deficit irrigation (DI) conditions (regulated deficit irrigation, RDI, and sustained deficit irrigation, SDI) but not in control almonds obtained from fully irrigated trees. Therefore, these results confirm PhytoPs and PhytoFs as valuable biomarkers to detect whether an almond-based product is hydroSOStainable. As a final conclusion, it can be stated that almond quality and functionality can be improved and water irrigation consumption can be reduced if controlled DI strategies are applied in almond orchards.