Here is an overview of what configuration of LC matching networks for RF applications you should use based on where on your Smith chart the load (antenna impedance) is located. Tricks: to place the series reactive element closest to where the resistance is lower. Since you know you also need a parallel reactive element, that comes furthest away from where the resistance is lowest. In most cases for HF / antenna / amateur radio applications the antenna resistance is higher than 50 ohms. However take care to correct for the impedance transformation that occurs along the feedline to the antenna.
Credit for the illustrations: VA3IUL
Here is VA3IULS PDF document: