In 1999, he became the first ever Brazilian player to sign for English club Arsenal, whom he signed for ahead of North London rivals Tottenham Hotspur who had made numerous offers for him. Before long he was first choice at left back, displacing long-time fan-favourite Nigel Winterburn. He had a setback early on in his first season when he missed a penalty in a shootout as Arsenal crashed out of the League Cup to Middlesbrough, and that season finished in similar heartbreak as Arsenal lost 4–1 on penalties against Turkish club Galatasaray in the 2000 UEFA Cup Final, although this time he did not take a penalty. During his second season at the club he was displaced by Ashley Cole. His stay only lasted for two years but in his short spell there he gained many friends and admirers and scored several spectacular goals including ones against Sheffield Wednesday, Charlton Athletic and Chelsea. He also scored twice in the Champions League for Arsenal against Sparta Prague and Spartak Moscow. In the 2000–01 season, Sylvinho was included in the PFA Team of the Year.