Mr. Monk and the Three Pies - S2-E11
Factual error: In this episode, when Sharona and Monk arrive to visit his brother, they talk about the swing set. Monk tells Sharona that his father put up the swing when he was 8 years old but this is a much newer swing set. Look at the curved plastic seats: these have come about in the last six to eight years. It also doesn't look at all rusty like a 40 year old swing would.
Suggested correction: Ambrose is obsessed with leaving the place "exactly the way dad left it for when he comes back." Hoarding old newspapers for him would be a character mistake, but things like keeping the old swingset maintained and up to current safety regulations so everything's perfect "when he returns" would be a thing he'd find to do around the house. His agoraphobia might not be so bad in the yard. Alternately, he could pay someone for yard upkeep, which would include the swingset.
Mr. Monk and the Sleeping Suspect - S2-E7
Continuity mistake: Monk throws the bomb into the toilet and shuts the door, pulling it towards him. When we see him hit by the blast there's no door in the way, and in the reverse shot looking into the bathroom the door has swung open into the room again, despite the blast radiating outwards. Plus it should have destroyed the door anyway.
Mr. Monk Goes to Jail - S2-E16
Continuity mistake: One of the times the prison guard is attempting to pat down Monk, his hands are approaching Monk's abdomen. After a cut to the next shot, his hands are suddenly around Monk's lower legs. (00:05:55)
Mr. Monk and the Captain's Wife - S2-E14
Continuity mistake: In the scene where Sharona returns the dog, she opens the gate, turns around and closes & latches the gate. They even make a point of showing the latched gate before she is on the porch. As she is talking to the owner, you see the gate behind her open and then closed between shots. She had latched it, so all scenes should have shown it latched.
Mr. Monk and the Paperboy - S2-E10
Continuity mistake: When Monk says "I can bench 200", you can tell he has his arms by his sides, but in the next shot, his hands are held up at the level of his waist. (00:12:15)
Mr. Monk and the Captain's Wife - S2-E14
Continuity mistake: In the pre-credits sequence, Karen attaches a clip to the right side of Leland's shirt, but a few seconds later, there is none on his right side. They are all on his left side. They also disappear and reappear.
Mr. Monk and the Captain's Wife - S2-E14
Visible crew/equipment: When Karen and Leland are arguing, a crew member is visible in the van's side window in the left of one shot.
Mr. Monk and the Paperboy - S2-E10
Deliberate mistake: When Sharona spots Disher's personal ad in the newspaper, there is a shot of it. She then reads the description of him from the ad, which matches what's on the screen, however, the second part she reads, "Seeks petite blond with no-nonsense attitude, kids ok" is not in the ad shown. (00:22:20)
Mr. Monk and the 12th Man - S2-E9
Other mistake: In the scene where Mr.Babcock is murdering the woman in the cinema, we see the woman has a big bucket of popcorn. As he starts strangling her, only a small amount of popcorn falls out. When the camera turns toward the floor there is a lot more popcorn on the floor and it it is spread right across the screen.
Mr. Monk Goes to Jail - S2-E16
Continuity mistake: The large blue Nazi/Swastika tattoo on the left side of the head Nazi's neck changes from being neat and symmetrical to uneven during the course of the episode. This is most noticeable when comparing the exercise-yard "you stole the watch" scene to the black-and-white "solving the case" flashback scene.
Mr. Monk and the T.V. Star - S2-E12
Continuity mistake: The blood stains on Brad Terry's sweatshirt change positions after he runs back into the house. A few shots later, they're suddenly so faint they're barely visible at all anymore. Blood stains don't fade, at least not in just a few minutes.
Mr. Monk and the Sleeping Suspect - S2-E7
Plot hole: Technically, Brian Babbage's plan would never have worked due to the fact that all outbound mail goes to a main post office from the local post office and then placed through scanners to determine the contents, which would have inevitably exposed the bomb inside.
Mr. Monk Goes Back to School - S2-E1
Character mistake: Sharona invites Monk home for dinner. Monk is playing with his food, and Sharona guesses it is because the potatoes are mixed together with the carrots. Sharona asks Kyle to fetch two plates (So Monk can separate the potatoes and carrots.) As he tilts the dinner plate, Monk succeeds in scraping all the carrots onto one dish - save for one stray potato - all the while speaking. He completes his thought without removing the stray potato. In all other instances, Monk cannot allow such a transgression. He either corrects it before saying his piece, or after. But he cannot let it go.
Mr. Monk Goes Back to School - S2-E1
Character mistake: When Kathy is presenting her model of General Robert E. Lee's surrender to General Ulysses S. Grant on April 9th, 1865, she incorrectly states that the surrender occurred "at the courthouse in Appomattox, Virginia." The surrender didn't take place at the actual courthouse, but rather at the McLean House, a private residence selected by Grant and his aides for the meeting of two of the greatest generals in American history. This is a common misconception as the village itself is called Appomattox Courthouse. (00:29:05)
Mr. Monk and the Sleeping Suspect - S2-E7
Character mistake: In Brian Baddage's house, when Randy says to the Captain, "ATF at 3 o'clock," they both look at 9 o'clock. (00:25:00 - 00:26:00)
Mr. Monk and the Sleeping Suspect - S2-E7
Factual error: After Monk has thrown the bomb into the toilet and the Feds arrive, Randy warns Stottlemeyer that the Feds arrive from 3 o'clock when in reality they are approaching them from the left, which would be 9 o'clock in "military terms." (00:25:04)
Mr. Monk Gets Married - S2-E15
Factual error: Disher gets the armoire open and recoils from the smell of the dead body inside, despite it being wrapped in plastic. But he somehow didn't smell it before getting the door open, despite it providing hardly any protection from a smell like that.
Mr. Monk Gets Married - S2-E15
Character mistake: Monk says West Virginia became a state after the Civil War, West Virginia actually became a state in 1863, during the Civil War.
Mr. Monk and the Three Pies - S2-E11
Continuity mistake: When Van Rankin takes the borrowed flour from his kitchen counter and hands it to Sharona, it's in a standard paper flour sack, and the counter is clean. Later, there's flour dust on the counter and the impression of a large, round flour tin - like the one in Monk's kitchen - instead of an imprint of the paper sack. (00:37:20)
Mr. Monk Goes to Mexico - S2-E2
Factual error: Monk states that one of the reasons he suspected Dr. Maduro was because the doctor stated the amount of fluid in the victim's lungs in pints, which meant the doctor had worked in the US. But even in the US, the medical profession uses the metric system.