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Urban encroachment into arable land along the peri-urban areas of Osun State, Nigeria prompted this investigation. The study is aimed at determining rate, pattern and effects of uncontrolled spatial expansion in the city. This study examines the trend in eight (8) peri-urban communities in Olorunda and Osogbo LGAs which were purposely selected. A multi-stage sampling technique was adopted in administering 230 questionnaires on randomly selected peri-urban farmers. Primary data collected were analysed using SPSS while Geographical Information Systems (GIS) data acquisition and sources were used to capture vegetation change, with 3 Landsat imageries sourced for the study. Findings revealed that 72% of interviewed farmers had a fear of losing their farmland to developmental projects as 16.1% of farmers had previously lost between 1 and 2 acres of farmland to such projects. Land modelling change detected that settlement/built-up-areas have increased from 978.03 hectares (6.60865%) in 1986 to 2976.39 hectares (20.11178%) in 2014, to the detriment of farmland/vegetative cover. As a result farmland/vegetative cover reduced from 9277.71 hectares (62.69045%) in 1986 to 7995.33 hectares (54.02527%) in 2014. The study discovered that such a degree of city encroachment and expansions into vegetative land cover is greatly impeding agricultural activities and farm production. Thus, the paper advocates that the government and land administrators formulate and implement policies in this direction.