Bennet was probably born into a prosperous family and received his first exposure to music as a choirboy. No doubt he had advanced instruction in music and by his early twenties had produced the aforementioned volume of 17 madrigals for four voices. At around that same time Bennet fashioned four psalm settings and a prayer for the 1599 Barley's psalter. Though Bennet's style showed the influence of Wilbye, Weelkes, and Dowland (Weepe, O mine eyes was almost certainly inspired by Dowland's Flowe my tears), his greatest debt was to Thomas Morley.
It is likely that Bennet had strong connections in high places in English society: many of his madrigals were written for festive occasions held at Court or in private residences of wealthy patrons in London. His madrigal Eliza, her name gives honour was one of several madrigals written for the feted guest at a celebration, in this case Queen Elizabeth. At such events, choirboys from the Chapel Royal were typically the featured performers.
Bennet probably wrote a fairly substantial number of madrigals and other vocal works, but few reached publication or survived in manuscript. Besides his 1599 efforts, he contributed a madrigal to the 1601 collection The Triumphes of Oriana, and composed six secular songs and an anthem for Ravenscroft's 1614 anthology A Briefe Discourse. It is likely that Bennet died in 1614 or shortly afterward.