Lipids in almonds are naturally encapsulated by cell walls which may reduce the actual metabolizable energy content of almonds. Oral processing increases the accessibility of lipids to digestive enzymes by grinding the almond matrix. This study aimed to investigate the effect of adding accompanying foods (chocolate and iceberg lettuce) to almonds on oral processing behaviour, bolus properties and predicted lipid release. Natural chewing times of four almond model foods including one almond (1.3 g), four almonds (4.6 g), one almond with chocolate (4.3 g) and one almond with iceberg lettuce (4.3 g) were collected from n = 59 participants in duplicate. Expectorated boli at the moment of swallowing were characterized for number and mean area of almond bolus particles. Predicted lipid bioaccessibility was estimated using a previously validated model. At similar bite size (4.3–4.6 g), the addition of chocolate and iceberg lettuce to almonds significantly decreased (p < 0.05) chewing time and significantly increased (p < 0.05) eating rate compared to consumption of almonds alone. Almond bolus particle sizes were similar for almonds consumed alone (one and four almonds) and with chocolate, while consuming almonds with lettuce generated significantly fewer and larger almond bolus particles (p < 0.05). Predicted lipid bioaccessibility of almonds consumed with iceberg lettuce was significantly lower (p < 0.05) than for almonds consumed alone (one and four almonds) and almonds consumed with chocolate. Eating rate correlated significantly and positively with the mean area of bolus particles and significantly and negatively with predicted lipid release. In conclusion, combining almonds with other foods such as chocolate and lettuce influences oral processing behaviour and bolus properties and consequently predicted lipid bioaccessibility of almonds, highlighting the impact of food matrix and consumption context on these aspects.