He has coached Emma Raducanu as well as guiding Dom Inglot and Robert Lindstedt to the US Open men's doubles semi-finals.

Cavaday played US collegiate tennis for North Carolina State University, amassing a 74-56 singles record and 74–53 in doubles, while studying for a degree in psychology.

[2] After finishing university, he turned professional and played regularly on the ITF Tour reaching a career-high of 1,022 in the ATP singles rankings, with his last match being in 2010.

[2][3] Moving into working with individual players, he coached Dom Inglot and Robert Lindstedt over the next two years, during which time they reached the men's doubles semi-finals at the 2015 US Open.

[2][3] Cavaday coached Aljaz Bedene from 2016 to 2018, helping him reach a career high ranking of world number 43.