Fall applications of synthetic nitrogen (N) fertilizers to cropland induces significant nitrous oxide (N2O) emissions during spring-thaw and throughout the growing season; impeding N2O gas reductions for the Canadian agricultural sector. A possible means to reduce N2O is with enhanced efficiency fertilizers (EEF) which are designed to delay the activity of urea hydrolysis and/or nitrification, or control the availability of plant inorganic N. The objective of this thesis was to quantify and compare cumulative N2O (ΣN2O kg N ha-1) and agronomic measurements of Canadian hard red spring wheat (Triticum aestivum L.) with EEF and non-EEF sources, and application timing (spring versus fall) in southern Manitoba. Treatments included fall and spring applications of granular urea with and without EEF containing urease inhibitor product- LIMUS, nitrification inhibitor product- eNtrench, double inhibitor product- SuperU, polymer coated urea- ESN, and anhydrous ammonia (AA) with and without a nitrification inhibitor- N-Serve. Using the static-vented chamber technique, treatments were examined in two replicated plot trials in each of three years from 2015 to 2017. Among five out of six sites which had an N source effect, eNtrench and SuperU reduced ΣN2O by 54 and 43%, respectively. Combining urea sources, the fall-applied ΣN2O was similar to spring at 4 of 6 sites. Precipitation events induced largest daily emissions from both fall and spring applications. LIMUS protein levels were 0.6 and 0.5% lower compared to eNtrench and ESN. No site observed a significant grain yield response to EEF sources. Grain yields and protein from fall applications were generally similar or lower than spring. eNtrench and SuperU were the most optimal products to reduce N2O and maintain agronomic variables. Future studies should investigate whether reduced EEF rates produce similar agronomic and environmental measurements as to this current study.