We analyse for the first time the CP violating ratio ε /ε in K → ππ decays in leptoquark (LQ) models. Assuming a mass gap to the electroweak (EW) scale, the main mechanism for LQs to contribute to ε /ε is EW gauge-mixing of semi-leptonic into nonleptonic operators, which we treat in the Standard Model effective theory (SMEFT). We perform also the one-loop decoupling for scalar LQs, finding that in all models with both left-handed and right-handed LQ couplings box-diagrams generate numerically strongly enhanced EW-penguin operators Q 8,8 already at the LQ scale. We then investigate correlations of ε /ε with rare Kaon processes (K L → π 0 νν, K + → π + νν, K L → π 0 ¯ , K S → µμ, ∆M K and ε K ) and find that even imposing only a moderate enhancement of (ε /ε) NP = 5 × 10 −4 to explain the current anomaly hinted by the Dual QCD approach and RBC-UKQCD lattice QCD calculations leads to conflicts with experimental upper bounds on rare Kaon processes. They exclude all LQ models with only a single coupling as an explanation of the ε /ε anomaly and put strong-to-serious constraints on parameter spaces of the remaining models. Future results on K + → π + νν from the NA62 collaboration, K L → π 0 νν from the KOTO experiment and K S → µμ from LHCb will even stronger exhibit the difficulty of LQ models in explaining the measured ε /ε, in case the ε /ε anomaly will be confirmed by improved lattice QCD calculations. Hopefully also improved measurements of K L → π 0 ¯ decays will one day help in this context.