Richardson competed in the singles draw of a Grand Slam three times, all at Wimbledon and on each occasions as a wildcard. In both 1992 and 1998 he lost in the opening round, to Marc Rosset and Hicham Arazi respectively. However, in the 1997 Wimbledon Championships he reached the third round, with wins over Spanish qualifier Sergi Duran in straight sets and then another Spaniard Juan Albert Viloca, in five sets. He was eliminated by countryman Greg Rusedski in the third round.
He was more successful as a doubles player, winning five tournament on the ATP Challenger Tour. One of those, at Seoul in 1995, was one with Tim Henman as his partner. The pair also reached the semi finals of the 1996 Czech Indoor tournament, an ATP Tour event. Richardson would later be a best man at Henman's wedding.
In 1997, Richardson represented an understrength Great Britain Davis Cup team against Zimbabwe. He defeated Byron Black in a singles match, to level the tie at 1-1 but his second match, against Byron's brother Wayne, which Richardson lost, was a dead-rubber, with Zimbabwe having already secured the tie.
|No.||Year||Tournament||Surface||Opponent in the final||Score in the final|
|1.||1997||Urbana, United States||Hard||Cecil Mamiit||6–7, 7–6, 6–3|
|No.||Year||Tournament||Surface||Partner||Opponents in the final||Score in the final|
|1.||1995||Seoul, South Korea||Clay||Tim Henman|| Filippo Messori|
|2.||1995||Rogaška Slatina, Slovenia||Carpet||Mark Petchey|| Patrick Baur|
|6–7, 6–4, 6–4|
|3.||1996||Bristol, Great Britain||Grass||Petr Pala|| Lionel Barthez|
|4.||1998||Lippstadt, Germany||Carpet||Myles Wakefield|| Raemon Sluiter|
|4–6, 7–6, 6–4|
|5.||1998||Lübeck, Germany||Carpet||Lorenzo Manta|| Stephane Simian|