Season 1989, Episode 1: Columbo Goes to the Guillotine - Psychic fraud Elliott Blake murders his former mentor, magician Max Dyson, by decapitating him with a rigged guillotine to prevent exposure and exact revenge for a past betrayal. Columbo investigates the seemingly accidental death. Ultimately, Columbo tricks Blake into attempting to kill him with the same guillotine, but the detective had secretly reversed the safety mechanism, leading to Blake's incriminating attempted murder and confession.

Season 1989, Episode 2: Murder, Smoke and Shadows - Hotshot director Alex Brady murders his childhood friend, Leonard Fisher, to prevent him from exposing Brady's role in the earlier death of Fisher's sister during a film stunt. Brady electrocutes Fisher on a rain-drenched movie set. Columbo meticulously uncovers the truth, using a hidden film and a studio tour ticket as key evidence. Columbo ultimately exposes Brady's elaborate cover-up, leading to his arrest.

Season 1989, Episode 3: Sex and the Married Detective - Renowned sex therapist Dr. Joan Allenby discovers her lover and business partner, David Kincaid, is cheating. She adopts an elaborate disguise as "Lisa" to lure and murder Kincaid at their clinic. Columbo investigates the perplexing case, eventually uncovering Allenby's meticulously planned revenge. He confronts her with evidence, leading to her confession of the murder driven by betrayal.

Season 1989, Episode 4: Grand Deceptions - Colonel Frank Brailie, embezzling funds and having an affair, murders Sergeant Major Lester Keegan to prevent blackmail. Brailie stages an alibi around a late delivery of military miniatures. Columbo meticulously proves Brailie switched delivery boxes, thereby discrediting his timeline. Columbo shatters Brailie's elaborate alibi, exposing him as a thief and murderer.

Season 1989, Episode 5: Murder, a Self Portrait - Artist Max Barsini drowns ex-wife Louise to silence her about his prior murder of art dealer Harry Chudnow. Barsini fakes an alibi, but Columbo exposes his deception. Using Louise's dream tapes and a paint speck, Columbo reveals Barsini's guilt, leading to his arrest for both crimes.