Mr. Monk and the 12th Man - S2-E9
Plot hole: Monk identifies the killer because of a shirt sleeve that gets ripped off... he noticed the button is sewed on in a unique manner with the threads parallel as opposed to the "standardized" crisscross pattern. The killer and Monk coincidentally use the same dry cleaner and Mrs. Ling sews buttons parallel because it's her style. Dialogue in the episode indicated she is the only one who sews buttons on like that. But I checked over 20 button up shirts here at my house and the ratio of crisscross to parallel button sewing methods is 50% of each - hardly some unique identification method.
Mr. Monk and the Very, Very Old Man - S2-E5
Continuity mistake: In the scene where Capt Stottlemeyer is vacuuming Monk's floor, you see the living room has wall-to-wall carpet. But just minutes later when they show the floor again, it is just a throw rug over hardwood floors. The room no longer has wall-to-wall carpet.
Suggested correction: It's never wall-to-wall carpeting. It's always a rug, and the Captain even calls it a rug. In the shot of the vacuum and the Captain's feet, you can see the hardwood floor behind him.
Earlier there was no rug at all. They were fighting about the coffee table and you could hear the scrapping noise of the coffee table on the bare floor.
Mr. Monk and the Very, Very Old Man - S2-E5
Continuity mistake: When Stottlemeyer moves the snake, the pinecone falls on the ground. The next scene, where Monk is on the table and talks to Stottlemeyer, the pinecone is back on the shelf. (00:25:26 - 00:26:36)
Mr. Monk Goes to Jail - S2-E16
Continuity mistake: When Monk and Sharona talk to Sylvia in the prison library the second time, the books on her desk change in various shots. At first, you see 3 piles of books, all with blue books on top. In the next shot the blue book closest to her is gone. In the next shot, she's straightening a red book next to her, but it goes back to being crooked.
Mr. Monk and the Very, Very Old Man - S2-E5
Continuity mistake: When the Captain is eating his sandwich while talking to Monk, the position of the sandwich and amount eaten keeps changing. He'll have it in his hand, but in the next shot it's on the plate. And you see him take a 2nd bite, but later only 1 bite has been taken.
Mr. Monk and the 12th Man - S2-E9
Visible crew/equipment: When Monk is talking to Dr. Kroger about Sharona's new boyfriend Kenny, you can see the cameraman's reflection in the window behind them. (00:09:26)
Mr. Monk Gets Married - S2-E15
Continuity mistake: In the room with the memoirs, Monk turns around and reaches towards a few slightly misaligned books to take one and read it. In the closeup, it's a neatly stacked shelf.
Mr. Monk and the Missing Granny - S2-E13
Continuity mistake: Monk identifies the kidnappers' house by the pizza box outside by the bin. In the wide shot it's upside down on its corner, with "zza" just visible behind a black bag. In the closeup it's turned around, so we can see more letters, and it's moved.
Mr. Monk and the Paperboy - S2-E10
Continuity mistake: Stottlemeyer says "does that make any sense to you?" as Monk is straightening the pots on the mantelpiece - all the lid handles are horizontal. The camera cuts away for a second, cuts back, and the lid on the far right has suddenly rotated 90°, whereupon Monk straightens it to be horizontal like the others.
Mr. Monk Gets Married - S2-E15
Continuity mistake: In Dalton's antique store, in the close of the forged map, the "sold" tag is covering part of the state names (mainly the West in West Virginia) and part of the picture. In the wide shot, the tag is now in the corner and not covering anything.
Mr. Monk Goes Back to School - S2-E1
Other mistake: Derek tells Beth to meet in their "usual spot" the next day at 8am. The next scene has Derek sitting at his desk and it looks like the kids are already in deep with their SAT tests. Beth falls at 8:25am (as per the clock in the testing room.) There is no way that Derek could have killed Beth, put her on the minute hand (later in episode on the Monk recap, it has 8:15am. If Derek was proctoring a SAT test, I don't know of any that start around 8:20 and immediately in depth.
Mr. Monk Goes Back to School - S2-E1
Factual error: In the cold opening, Derek said that his wife is very smart and got a 1680 on the SAT. This episode takes place in 2003, the writing portion that was added to make the max (2400, not 1600) was in 2005.
Mr. Monk Goes to Jail - S2-E16
Factual error: The murdered man is killed by poison while having his last meal just before they execute him that night. Death row inmates have their last meal one to two days before they're executed.
Mr. Monk and the Sleeping Suspect - S2-E7
Character mistake: Brian Babbage is such a perfectionist and plans out such an elaborated plan for his crimes that it is very unlikely that he would simply leave the ketchup bottles sticking to the ceiling for the police to be found after he had timed the perfect glue for his plan. Plus, he even had staffers who already knew about the bottles and it would have taken him not more than a single order for the bottles to be removed. (00:23:50)
Mr. Monk and the T.V. Star - S2-E12
Plot hole: Unless I missed something, the killer didn't wipe his prints off the knife he used to kill his ex-wife.
Mr. Monk Goes Back to School - S2-E1
Continuity mistake: Mr Monk completes his name on the chalk board at the beginning of class, but when class is dismissed the 'k' in Monk is incomplete.
Suggested correction: After he wrote his name, he says "what's up with that k?" and erases it. He started to re-write the k when he got hit by the eraser, leaving it unfinished.
Mr. Monk and the Three Pies - S2-E11
Continuity mistake: When Van Rankin shoots his wife, the black gym bag, which has been slung over his shoulder since he entered the kitchen, disappears between shots. (00:31:05)