After winning the title of the
men's doubles of the
Nottingham Open alongside
Jacob Fearnley, the pair received wildcards for the
2023 Wimbledon Championships. He was also given a wildcard into the men's qualifying singles and beat
Mili Poljicak before pushing the experienced
Radu Albot to three sets. In the doubles, he and Fearnley beat
Andre Goransson and
Ben McLachlan in the opening round before losing to
Matthew Ebden and
Rohan Bopanna. He won three consecutive singles titles on the ITF tennis tour in October 2024. He began 2025 with another title at that level in
Sunderland before adding a fifth in six months in
Bakersfield, United States in March 2025, defeating American Alex Rybakov in the final in straight sets to seal the title. In June 2025, Monday was awarded a wildcard to make his major tournament main-draw singles debut at
Wimbledon, where he lost to 13th seed
Tommy Paul in the first round. In September 2025, Monday combined with
Patrick Harper to win the doubles title at the
Columbus Challenger, defeating
George Goldhoff and
Theodore Winegar in the final. ==ATP Challenger and ITF World Tennis Tour finals==