According to an article in The Scotsman, Smith is suing the pair over a pension fund that was set up while he was managing Everton in the 1990s.
The case follows former Premier League footballer Colin Hendry saying on 5 June he will be seeking compensation if an investigation into Kingsbridge Asset Management proves its staff conspired to defraud a large number of its high net worth clients.
Smith alleges Caisley and Alexander agreed to return £600,000 ($801,286, €684,988) they received in commission on “financial products” but only paid him £280,000.
Smith’s legal team now wants the court to rule that the two advisers should pay their client the remaining sum.
When the case was called at the Court of Sessions in Edinburgh on 5 June, it was revealed that Caisley is no longer contesting the legal bid, but Alexander is still fighting it, reports The Scotsman.
Alexander’s lawyer, David Thomson QC, said Smith and his client had a meeting in December 2013 where certain matters were agreed.
Further, Thomson asked the judge for access to documents from Smith’s legal team in order to prepare for the case.
However, Smith’s lawyer said no agreement was entered in 2013 and the document request was “classic fishing”.
A full hearing is set to be held later this month.