[2] By 2003, Sherwood had acquired a reputation for a lackadaisical attitude, a party loving life style and negatively influencing younger players.

While at a Jamaica Futures event in November 2003, Sherwood delivered an on-court barrage at his Lawn Tennis Association coach.

Back in the UK, he missed a training session claiming he was ill, despite living five minutes away from the LTA's headquarters with an on-site doctor.

[3] In March 2005 Sherwood played doubles with Andy Murray in their joint Davis Cup debuts for the Europe/Africa Zone Group I match against Israel.

[7] In September 2005, at the World Group Play-off against Switzerland, Sherwood was beaten in the first singles dead rubber, with Great Britain losing 5–0.