Bailey's highest points total in a season came in the Premiership season of Winter 2009, playing with the Lasers in Under 12 Division 2, Bailey scored 116 points from 17 games at an average of 6.9ppg. Throughout his career, Bailey has recorded 20+ points in a game on 1 occasion. Bailey has scored 10 or more points in a game on 10 occasions, with his career high of 20 points occurring in 2009.
In 15 finals games, Bailey has scored 24 points. Bailey has scored 14 points in his 4 Grand Final appearances.
Bailey's 50th career game was played in Round 2 of Spring 2005. Playing for the U10 Jets, Bailey did not score in the Jets 6-30 defeat. Bailey's 100th career game occurred in Grading 2 of Autumn 2007. As a member of the Under 12 Comets, Bailey scored 6pts as the Comets won 26-11. Game 150 occurred in Round 15 of Spring 2007. Bailey scored 8pts in the Comets 22-24 defeat. Bailey became one of the youngest players in club history to reach 200 career games. Bailey's 200th game was played in the Preliminary Final of Summer 2008/09 and at the age of 10. The Comets, in Under 12 Division 1 would win through to the Grand Final, with 2pts from Bailey in the 44-36 win. Evidently, Bailey would also become one of the youngest players in Woodville history to also reach the 250 Game milestone. Bailey played Game 250 in Round 9 of Summer 2009/10 with the Under 14 Comets. Bailey did not score in the Comets 36-27 win on Saturday, November 14th, 2009.
On Saturday, April 2nd 2011, Bailey became the 13th player to reach the 300 Game Milestone for the Woodville Basketball Club. The game itself was the 2nd Semi Final of the Summer 2010/11 season, with Bailey scoring a team high 8 points as the Under 14 Division 3 Meteors won through to the Grand Final with a 14-13 win over Cambridge.
Bailey took part in the Inaugural 2009 Greater Geelong Tournament with the Under 14 Comets. At Geelong, Bailey played 3 games.
Over Bailey's career, which is still currently active with the Under 14 Wizards, a career now spanning 7 years, Bailey has played for 12 WOODVILLE teams. He has played for the WIZARDS, RUGRATS, WONDERS, JETS, SHARKS, COMETS, WOLVES, JAGUARS, ENERGY, MAGIC, LASERS and METEORS, ranging in age groups from under 8's through to under 16's. Bailey has played in four grand finals, coming Runners Up in Autumn 2007 (Under 12 Comets) and Summer 2008/09 (Under 12 Comets) with a Premiership success coming in Winter 2009 (Under 12 Lasers) and in Summer 2010/11 (Under 14 Meteors). Now in his 25th season, Bailey has scored more than 100 points in a season on 2 occasions.