The present study aims to analyse the land market trend with particular reference to the main typologies of crop in Sicily (1992-2010). More specifically, after examining the trend in agricultural land average prices, both in current and constant terms, the dynamic formulation of Shift and Share Analysis (DSSA) was carried out, in order to check the growth gap between the average prices in the Sicilian provinces and the correspondent regional ones over the period, and trying to identify its causes also on the basis of the relationship between land values and the agro-food markets dynamics in the investigated period. The analysis of average land values shows a positive trend in current terms, but a steady erosion in constant values. The application of DSSA highlights that the average land values expressed in current prices have a positive market dynamics (except for the province of Palermo), but lower than the overall regional trend, whereas Agrigento and Ragusa growth rates are higher than the regional one. On the contrary, the analysis in real terms shows a heavily erosive dynamics of provincial average prices which is more marked than the overall regional one, with the exception of Agrigento where the negative growth rate is lower than the overall trend. The analysis also measured the growth differential between the dynamics of the average values for each crop typology and the overall regional trend. More specifically, the study pointed out the dichotomy characterising the Sicilian land market in the period 1992-2010: on the one hand, the positive data of arable and horticultural crops and, to a lesser extent, permanent grassland due to a good structural framework capable of absorbing the shortcomings at local level, on the other hand, negative growth differential recorded for tree crops, due almost exclusively to substantial structural weaknesses.