In her spare time of late, she plays on the touchtennis tour against amateurs and other professional tennis players for fun.

Webley-Smith also has her own column in the magazine tennishead in which she often covers the financial aspects of being a mid- to low ranked tour player.

Problems with Webley-Smith's right ankle began in 2002 when she broke it whilst on court competing in the qualifying tournament for the $25k ITF Circuit event in Cardiff and underwent surgery to repair both the bone and the damage caused to the ligaments.

However, she had to take yet more time out later in 2005 when she began experiencing sharp pains in the same ankle while warming up for an ITF tournament in Puebla, Mexico.

[5] In 2009, she also began to have trouble with her wrist after injuring it during an ITF event in Tanjung Selor in Indonesia, just a number of weeks before Wimbledon.

She competed at Wimbledon juniors a total of four times; in 1999, 2000 and 2001 she lost in the qualifying stages but in 2002 she reached the second round of the main draw.

[9] The 2001 season began for Webley-Smith with qualifying and reaching the quarterfinals of the $10k event in Jersey, before being beaten by Anne Keothavong, 6–3, 7–6.

But for the rest of the year, she lost in the qualifying stages in every other tournament she entered with the exception of the Sunderland event where she was defeated again by Keothavong, 6–3, 6–4.

She also played in the main draw of her final ITF tournament of the year as a lucky loser but was again beaten in round one.

[9] Webley-Smith had a varied year in 2002, with limited success on the ITF Circuit but also her first appearance in a Grand Slam tournament at Wimbledon where she lost in the first round of qualifying to Nina Dübbers, 1–6, 2–6.

[9] Webley-Smith played her first professional match since breaking her ankle in 2002 in April at the qualifying event for the $10k tournament in Bournemouth where she lost in the second round.

In June, for the first time in her career, she was given a wildcard into the Birmingham Classic qualifying draw, a Tier-III tournament; she was beaten by Bethanie Mattek in straight sets, 6–3, 6–4.

Two more consecutive quarterfinal appearances in ITF tournaments immediately followed this, Waco, Texas ($10k) and Vancouver ($25k), and one more in August in a $10k event in London.

In this same tournament, she reached the doubles final partnering compatriot, Chantal Coombs, and lost to Martina Müller and Vladimíra Uhlířová, 6–7, 3–6.

In her first ever main-draw Grand Slam appearance, she managed to survive rain delays and defeat Frenchwoman Séverine Beltrame, in straight sets, to reach the second round[2] where she faced 31st seed Amy Frazier.

She continued competing on the ITF Circuit for the first half of the year and reached the quarterfinal stages in two more $10k tournaments, in Tampico, Tamaulipas and Ho Chi Minh City.

[9] She spent much of the 2006 season out of action due to suffering from septicaemia as a result of her long-term ankle problems which began in 2002.

[9] In February 2009, Webley-Smith returned to the ITF Circuit and in March she won the first singles title of her career in Spain by beating Elena Chalova in the final, 6–0, 7–6.

Returning to the tour in mid-June, Webley-Smith was given a wildcard into the qualifying tournament at Eastbourne where she lost 0–6, 6–7 to María José Martínez Sánchez.