Monaco successively entered into a coaching career, serving as assistant coach of Lucchese during the 2000–01 season and then as Ascoli's youth coach until 2005. In July 2005 he took his first head coaching job at Serie C1's Lanciano, then working as head coach of A.C. Ancona from July to December 2006, and again from March 2007 to May 2009, leading the biancorossi to promotion to Serie B in 2008, before being sacked due to poor results in May 2009. His successive coaching experience was at the helm of Potenza on Prima Divisione, where he replaced Ezio Capuano for a bare month (from September to October 2009).
