 Nyorera kuenderera kweiyi ndima - Pakati pemwaka wa1999-2000 Guidolin akabatana neSerie A divi Bologna, yaimbove kirabhu semutambi. Pasinei nokupedza wechipfumbamwe mumwaka wapfuura, Bologna akanga akakodzera 19992000 UEFA Cup mushure mekukunda tie-breaker kurwisa Internazionale. Guidolin akavatora kuenda kunhanho yechitatu yeEFAFA Cup, kwavakabviswa neGalatasaray. Mumwaka weSerie A, vakapedza vari pachinzvimbo chegumi neimwe. Mushandirapamwe weligi wakatevera wakapera neimwe nzvimbo yechipfumbamwe, ichiteverwa neimwe diki yekuvandudza kunzvimbo yechinomweuye kupinda mumutambo wezhizha, 2002 UEFA Intertoto Cup, uko vakakundwa mumitambo mitatu yekupedzisira naFulham. 