[1][2] Maddy left school to join Leicestershire aged 17[3] and made his senior debut for the county towards the end of the 1993 English cricket season in a one-day match against Derbyshire at Grace Road.
He made his first-class cricket debut the following season and played regularly for Leicestershire between 1995 and 2006.
[4][7] Maddy scored over 13,000 runs and took more than 250 wickets in first-class county matches during his domestic career as well as scoring over 9,000 runs and taking over 220 wickets in one-day county cricket.
[7][10][11] In May 2022, Maddy was named as the coach of the Croatia national cricket team, ahead of their ICC Men's T20 World Cup Europe Qualifier matches in Finland in July 2022.
[12] In 2013 Maddy took up a coaching role at Solihull School as Master in charge of Cricket.