The hole injection in Schottky barriers formed between p-type doped regioregular poly(3-hexylthiophene-2,5-diyl) (rr-P3HT) and silver (Ag) is investigated. The rr-P3HT is controllably doped using the acceptor 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ). We demonstrate that only one order of magnitude increase in the background hole density p0, from 2×1016 to 2×1017 cm−3, enhances the hole injection with two orders of magnitude. The hole injection barrier is lowered by 0.5 eV and exhibits a linear dependence on p0, which can be explained by doping induced surface charges.