Inta lagu guda jiray waqtigiisa kooxda, heerka shaqada ee Gattuso iyo dabacsanaanta sida kubbadda-guusha ayaa markii dambe u oggolaatay tababaraha Milan Carlo Ancelotti inuu dhigo ciyaaryahanka khadka dhexe ee Andrea Pirlo isaga oo leh hal abuur badan, weerar, halka Gattuso uu ku taageeray door qoto dheer, oo ah daafaca dhexe; iskaashigan khadka dhexe wuxuu muhiim u ahaa guulaha gudaha iyo dibedda ee Milan ee Ancelotti, oo ay ku jiraan Coppa Italia, UEFA Champions League iyo UEFA Super Cup sanadkii 2003, iyo sidoo kale horyaalka Serie A iyo Supercoppa Italiana
sanadkii 2004. Gattuso wuxuu heshiis dheerayn la saxiixday Milan bishii Juun 2003 iyo Oktoobar 2004. Intii lagu jiray muddadan, Gattuso wuxuu sidoo kale gaadhay 2005 UEFA Champions League Final Milan, kaliya waxaa laga badiyay Liverpool rigoore, ka dib markii markii hore ay hogaanka u haysay 3 <unk> 0 waqtiga nasashada.