Steven Stewart, 45, took Leslie Marelic, 26, to Perth Sheriff Court to recover the price of a pair of Christian Louboutin shoes and a Louis Vuitton handbag.
He sued her over claims he had bought the luxury items on his credit card but expected to be repaid as he considered the money to be a loan.
The boss of Perth-based Chas Stewart Plumbing won his case at the city's sheriff court yesterday, but was attacked by a sheriff for acting out of "malice" to claim back money he did not need.
Sheriff William Wood said: "It's quite clear this current dispute has been borne out of a failed relationship. Mr Stewart recognised that if there had been a reconciliation no claim on the monies would have been made.
"The undisputed evidence was the relationship had been stormy. Miss Marelic said she regarded the relationship as being controlling. None of which explains why she continued to invest in it.
"I don't think it speaks particularly highly of Mr Stewart that he has sought to pursue this loss for what, to Miss Marelic, is a considerable sum. From reading your credit card statements, Mr Stewart, this is not a particularly considerable sum.
"This matter has been borne out of malice to a certain extent, but that does not mean the money is not due, and I find that it is due."
The court was told Miss Marelic, now a supermarket manager, had been earning minimum wage working for Mr Stewart's Perth-based firm when they got involved in an 18-month relationship.
The relationship had been rocky at the start of 2012 and Mr Stewart arranged a romantic weekend at the five-star Sheraton Grand spa hotel in Edinburgh to attempt a reconciliation.
During the trip he used his card to buy the £565 Louboutin shoes from Harvey Nichols and an £890 handbag from Louis Vuitton.
He said: "We usually went to Harvey Nichols for a couple of glasses of wine and a bit of shopping. She saw a couple of items she liked and asked if I would give her a loan. It was certainly not a gift. She offered to pay me back at £50-a-week from her wages because she was working in the office. I got her to sign a bit of paper.
"I asked her to write on Sheraton headed note paper in the room that she would pay me back and she signed it. I just want the money back for the loan we agreed."
Ms Marelic claimed she had been "terrified" of the businessman and had contacted the police.
Sheriff Wood said, legally, there was a presumption against "gifts" and it was for the recipient to prove an item had been gifted.
She said: "When you give someone a gift, it's a gift. It's ridiculous to ask for it back"
Miss Marelic was ordered to pay her former lover £1001. Mr Stewart initially sued Miss Marelic for £1445 pounds in a small claims action, but the sum was revised down to account for withheld wages and a sum she handed to him.