Background: The preexistence of obesity with nutritional anaemia is becoming an increasing problem in the Eastern Mediterranean Region (EMR). Much controversy exists around the role of continued breastfeeding in alleviating the health and survival consequences of these problems in the region. Aim: To examine trends and relationships of nutritional anaemia (NA) in women and children under-five years of age (CU5) with obesity and breastfeeding practices in the EMR. Methods: Data from regional database banks of WHO and UNICEF for anaemia in pregnant and non-pregnant women and CU5 from 22 countries in EMR were retrieved, compiled, and statistically analyzed. Breastfeeding indicators for timely first suckle (TFS), exclusive breastfeeding (EBF) and continued breastfeeding for 12 (BFC12) and 24 months (BFC24), low-birth-weight (LBW), stunting, overweight, total fertility rates (TFR) and mortality rates (MR) were correlated with nutritional anaemia and analyzed by income groups into 5 low income countries (LIC), 11 middle income countries (MIC) and 6 high income countries (HIC). Results: Trends in mean prevalence of anaemia in women showed a concave curve increasing after a short decrease in the early 2000 in all income groups (P > 0.05). Trends in anaemia in the CU5 exhibited a steep decrease from a mean of 52.59 ± 16.4 in 2000 to 37.3 ± 14.9 in 2016 at P < 0.002, the steep decline was significant in HIC (P < 0.01) and MIC (P < 0.02), but not for LIC (P > 0.05). Anaemia prevalence in women and CU5 was significantly correlated to LBW, stunting, and with overweight and obesity in adults but negatively in CU5. All age specific MRs were highly correlated with anaemia in pregnant, non-pregnant and CU5 at P < 0.001 and TFR at P < 0.05. BFC for shorter durations was negatively correlated with anaemia in pregnant women (r-0.5) at P < 0.05 and was positively correlated in MIC and HIC. In non-pregnant women, BFC12 and BFC 24 correlated positively with anaemia prevalence in all three income groups at P < 0.01. Conclusions: Completing optimal breastfeeding for two years should be promoted to protect women and CU5 from anemia and obesity. Nutritional anemia during pregnancy increases regional rates of LBW, stunting and mortality. Spacing out births by encouraging longer duration of breastfeeding, to replenish iron stores, can help alleviate many of the health and nutritional problems in the region.