Bennett moved to Villa from Middlesbrough back in 2012, but he has struggled to make an impression at the Midlands side.
The left-back played just once of the Claret and Blues last season, and was sent out on loan to both Bournemouth and Sheffield Wednesday.
Bennett’s future at Villa looked very uncertain going into the summer transfer window, however, he is reportedly winning over Di Matteo.
Villa’s coaching staff are said to have been very impressed by Bennett’s showings in training, with his set piece delivery catching the eye.
Bennett’s strong form was taken into Villa’s first pre-season friendly of the season, as he scored during an 8-0 victory.
Bennett now looks likely to stay at Villa, and he could yet have an important role to play as the Midlands side aim to bounce back immediately from last season’s disappointing relegation.