Craig Jaret Hutchinson was convicted in December 2011 and sentenced to 18 months in prison after his trial heard he sabotaged all of his girlfriend's condoms with a pin in 2006 in a bid to salvage his relationship with the woman, who cannot be identified.
He thought if she got pregnant, they would stay together.
In a majority decision released Thursday, the Nova Scotia Court of Appeal noted: "Mr. Hutchinson began encouraging her to take a pregnancy test. She wondered why but, after much persistence, she acceded to his request. It came back as negative," the court wrote.
"This was September 1. He insisted that she take another. She did so on September 5. It came back as positive. She was shocked. He was delighted."
It was only after the positive pregnancy test that Hutchinson admitted to the sabotage. Things did not turn out as he'd hoped — his Halifax-area girlfriend broke off the relationship, called police and had an abortion.
She later suffered an infection of her uterus that was treated with antibiotics.
Hutchinson, of Clyde River, was initially charged with aggravated sexual assault but that charge was dismissed at his first trial. He was eventually retried and convicted of sexual assault.
Hutchinson filed an appeal, arguing the Nova Scotia Supreme Court's sentence was harsh and excessive and that the woman voluntarily consented to having sex with him.
The case went before the Nova Scotia Court of Appeal and hinged on the issue of consent. The court ruled the sentence was not unfit and the trial judge was correct to conclude Hutchinson's girlfriend had consented to sex, but not unprotected sex.
Hutchinson was granted bail pending his appeal and is back in custody.
The case may not end here, however. One justice on the Court of Appeal would have granted Hutchinson's appeal, and the fact that there was a dissenting voice means Hutchinson has an automatic right to appeal this ruling to the Supreme Court of Canada.
Hutchinson's lawyer, Luke Craggs, told CBC News no decision has been made on an appeal.