Old Boys' is a regular entrant to the Chatham Cup, recording its best season in 2009, when it reached the last 32 stage of the competition.

It currently plays in the Donald Gray division, the premiere men's football grade in Southland.

The team has won the Southland Region's Donald Gray Memorial Cup on six occasions.

With close to 300 registered junior and senior players Old Boys' has become the largest football club in Southland.

Old Boys' subsequently won the match, and were promoted back to the third tier of NZ football for the first time since the mid 2010's.