As a student at the University of Otago he shared a flat with fellow former All Blacks Anton Oliver and Tony Brown and earned the nickname 'Donk'.

In 1999, with Maling in good form, the Highlanders reached the Super 14 final where they were narrowly defeated by the Canterbury Crusaders by a score of 24–19.

During most of this time he was one of the Highlanders key players, playing at lock, and known for his energy, reliability in the line out, and good work rate.

However, at the end of the 2004 season the New Zealand Rugby Almanack commented that "Simon Maling lacked the enthusiasm of earlier in his career".

[3] In 2006, Suntory Sungoliath lost the final of the Top League and Microsoft Cup title to Toshiba Brave Lupus by a score of 33–18.

Then in February 2007, Suntory Sungoliath again lost the final of the Top League and Microsoft Cup title to Toshiba Brave Lupus before a crowd of 23,076 at Tokyo's Chichibunomiya Stadium, the first sellout at the ground in 10 years.