In the 2009–10 season, Robertson again started as a regular, featuring in the first four matches of the season before being sent off in the 1–1 draw at Celtic. In October the Dundee director, Calum Melville, publicly stated he was planning to bid £500,000 for the Scotland international in the January transfer window. United, however, were not impressed and threatened to haul him in front of the SFA over these comments. Craig Levein, the United manager, criticised the Dundee director by suggesting he needs tutored in the workings of football. Dundee manager Jocky Scott was also reluctant to sign Robertson, especially not in the near future. During the season, Robertson suffered various injuries, mostly an Inguinal Hernia, which ruled him out for the remaining few months of the season before making his return in late-April against Motherwell. Robertson came on as a substitute in the 2010 Scottish Cup Final win, picking up his first winners medal. After the match, Robertson talked about winning the final and said "It's been a long 18 months and while the Cup Final doesn't make up for all the frustration and pain that I went through, it helps quite a bit. And I'm proud to have played a part in this win and somehow got a winner's medal that I never dreamed could have come my way two months ago.". Shortly after, Robertson signed a 12-month contract extension, that will expire in 2012