Structured emulsions, including monoacylglycerol (MAG) gels, are of interest as alternatives to shortenings rich in saturated and trans fatty acids (SFA and TFA). However, an understanding of their physical and nutritional functionality in baked products is limited. The objective of this randomized crossover study was to compare the postprandial lipid and glucose responses to two different baked product matrices produced with a MAG gel. Differences between study treatments are discussed in the context of underlying ingredient interactions impacting, primarily, starch digestibility. Healthy males (n = 18, 19-40 years, BMI ≤27 kg m-2, waist circumference ≤102 cm, fasting plasma glucose <5.6 mmoL L-1, insulin <180 pmol L -1 and TAG <1.7 mmol L-1) attended six study visits, each separated by at least one week, and consumed one of six study treatments with subsequent blood sampling for 6 h for determination of triacylglycerol (TAG), glucose, insulin and free fatty acids (FFA). The study treatments consisted of sugar-free cakes and cookies (high and low moisture products, respectively) produced using either the canola oil-based structured MAG gel or the compositionally-equivalent MAG gel ingredients. Although MAG gel structure per se did not impact postprandial response, all cookies had higher TAG responses compared with cakes, even when matched for fat content. Sugar cookies containing 40 g of the MAG gel or an industry standard stearic-rich shortening were also compared, with no differences observed in postprandial response.