He played his first top-level tournament at the 2004 IRTPA Championships at The Oratory School, defeating Craig Greenhalgh in qualifying, but losing to Ricardo Smith in the first round.

His breakout season continued at the 2009 IRTPA Championships at Manchester, reaching the final for the first time losing to World Champion Robert Fahey.

After defeating Chris Chapman and Ruaraidh Gunn in the semi final, Taylor-Matthews and Snow lost to Robert Fahey and Steve Virgona 5 sets to 0.

At the end of the 2012 season, Taylor-Matthews moved to a role as Senior Professional at Hatfield House Real Tennis Club in Hertfordshire.

[5] Taylor-Matthews next highlight was reaching the final of the 2014 and 2016 Australian Opens, losing to Robert Fahey in straight sets on both occasions.

His next breakthrough was at the 2018 French Open, where he won the doubles competition with John Lumley, defeating Steve Virgona and Chris Chapman in the final in 5 sets.

During the Eliminator process and subsequent pandemic, Taylor-Matthews started a real tennis themed podcast with fellow player Robert Shenkman called "A View From the Hazards".

By the middle of the year, he had recovered his form enough to reach a third consecutive Champions Trophy Final, losing to Nick Howell.

Taylor-Matthews started 2025 by reaching the semi final of the Australian Open, losing in an upset result to Kieran Booth.

He reached the doubles final playing with Robert Fahey, losing to Camden Riviere and Chris Chapman in five sets.