On September 13, 1999, Spadea achieved a top 20 ranking for the first time. However, from October 1999 to June 2000, Spadea suffered a record losing run of 21 losses in a row. His losing streak led the Associated Press to dub him "the Charlie Brown of tennis" . He ended the streak in the first round of 2000 Wimbledon with an opening round 6–3, 6–7, 6–3, 6–7, 9–7 win over 14th seed Greg Rusedski, in a five-set marathon, which lasted for nearly four hours. Spadea's world ranking fell as low as 237 on October 23, 2000.