Robertson then moved to Dundee, where he had loan spells at Brechin City, Inverness Caledonian Thistle, and Ayr United.
Robertson represented Scotland at the under-21 level, finalising his career following his transition into a managerial role with Culter.
However, in 2000, Robertson once again gradually found his first team opportunities limited and he spent two months on loan to Ayr United before he was signed by Neale Cooper for Ross County in February 2001.
Robertson formed a strong relationship with manager Neale Cooper and he found himself playing regular football for the next three years.
Despite his popularity amongst the Ross County fans, Hugh Robertson decided to follow his former manager Neale Cooper and signed for Hartlepool United in January 2004.
Not to be deterred, Robertson retook the free kick and scored, placing the ball in almost an identical position.
Robertson continued scoring from free kicks and long distances and this earned him cult status amongst the Hartlepool fans who began calling him "Hugh the Hammer".
[citation needed] Robertson started the 2004–05 season in much the same fashion and scored another free kick against Bradford City on the opening day.