Following a successful pre-season with the Madrid team in Switzerland and Italy, McManaman and the team then returned to Spain and he proved an instant hit with the fans at the Santiago Bernabéu Stadium after scoring three times and creating several goals in his first few games for "Los Merengues". McManaman made his debut for Madrid on 22 August 1999 in the 2–1 La Liga win over Mallorca at the Son Moix stadium, Mallorca, where he assisted Fernando Morientes in scoring an injury time equaliser, enabling Madrid to go on to win 2–1 with seconds remaining. He scored his first goal for the club a week later on his home debut on 29 August in a 4–1 thumping of Numancia at the Santiago Bernabéu.