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Frail began his career with [[Archie Knox]]'s [[Dundee F.C.|Dundee]] in 1985, gradually developing into a first-team player by the end of the decade. He helped the [[Dens Park]] side to victory in the inaugural [[Scottish Challenge Cup]] in [[1990–91 in Scottish football|1990–91]], however his progress was hindered by a serious [[knee]] [[anterior cruciate ligament|ligament]] injury, causing him to miss almost an entire season.<ref name="rivals">{{cite news|url=http://tranmererovers.rivals.net/default.asp?sid=930&p=2&stid=8377097|archive-url=https://web.archive.org/web/20051115080202/http://tranmererovers.rivals.net/default.asp?sid=930&p=2&stid=8377097|url-status=dead|archive-date=15 November 2005|title=Where are they now? Stephen Frail|publisher=RoversRearGuard|access-date=6 April 2007}},</ref>
Frail joined Hearts in a £130,000 deal in March 1994 and his form during the [[1994–95 in Scottish football|1994–95]] season as a right wingback led to media speculation of a call-up to the [[Scotland national football team|Scotland national side]].
Unable to maintain a permanent position in the team he filled-in as a defensive midfielder when required as well as deputising for Locke but left [[Edinburgh]] for [[Merseyside]] when [[Tranmere Rovers F.C.|Tranmere Rovers]] paid £90,000 for his services in January 1998.
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