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Audio/visual unsynchronised 

At the bar after the first tournament, when Happy says "I was on this tour for one reason: money" when the camera shows the back of his head, his mouth is not moving.
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Character error 

At the AT&T Open, Shooter asks his caddy for advice, the caddy gives it and Shooter ignores it by choosing a different club. Right before Shooter takes his shot the caddy moves forward and to the right, which places him directly in Shooter's eye-line. This would never happen - all caddies know they must stand behind the golfer as to not obstruct him.
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Shooter has a chip shot where he is in the rough with very little green to work with. His caddy recommends he use a 5-iron. There is no way any golfer from any walk of life would use a 5 iron to hit that shot, as it would require a club with much more loft. The idea that Shooter's caddy would even suggest it shows that he knows absolutely nothing about golf, which brings up the question 'how did he land a job on the pro tour, with one of the best players, no less?'
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Continuity 

At the hockey try-outs, the coaches are shown standing behind the glass right after Happy shatters it with his slap shot.
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At the beginning when Happy is playing hockey, he hits the puck at the glass which the two men are standing behind. The glass clearly gets broken but then in the next close-up shot of the two men, the glass is back because a reflection can be seen in it.
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When Happy is signing the woman's chest, the 'Gilmore' section of the signature moves from one side of the chest to the other.
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The golf ball hit at Gilmore's grandmother's house passes by more cars than were seen on the driveway previously.
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Grandma's bag disappears from under her nursing home bed.
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During the first hole of the Waterberry Open, Happy's ball moves from the back to the front of the green.
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When Happy says he is sorry to Chubs asking for his forgiveness, and shakes Chubs' hand breaking off all his wooden fingers, Happy then picks all the fingers up. But when he picks up the pinky finger, he places it in Chubs hand with his left hand, and when the scene flashes back Happy is placing it in Chubs hand with his right hand.
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The Subway logo on the PR woman's soda mug moves between shots.
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When Happy is introduced to the members of the Gold Jacket Club, Shooter's glass repeatedly switches hands between shots.
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Shooter's club switches hands during the "somebody learned to put" sequence.
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When Happy lands his "final putt", the crowd behind him runs to congratulate him, and there is a girl wearing a baby blue t-shirt patting him on the back. This same girl is seen in the next shot of Happy's supporters clapping for him on the sidelines.
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When Happy and the woman are at the hockey rink and she shots the puck. It crosses through the crease twice
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When Happy backs the car into the trash can, he puts his arm out the window as he leans out to talk. In the next shot, his arm is inside again.
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When Mr. Larson grabs Shooter's golf club out of the bag and bends it in half, he grabs the head of the club with his left hand and the handle in his right. In the next shot looking through the curve of the club at Shooter, the golf club has switched directions with the head of the club in his right hand and the handle in his left.
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When Happy and Bob Barker are fighting, people in the crowd move to different spots in the row during each shot.
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When Happy is "fixing" the air conditioning and it falls, it has a wood frame around it so it can fit in the window. In the next shot where the Mista-Mista lady is crushed by it, the frame is gone.
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When Happy and Shooter are at the club right after the first game of the tour, Shooter's martini has 2 olives in it. Afterwards when he gets it re-filled, there are 4 olives. In the next shot however, when Shooter tells Happy not to turn his back on him, he has only 1 olive in his martini glass.
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Happy's Plymouth Duster has a sunroof when the lady from the nursing home jumps on the hood. In other scenes the sunroof is missing.
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When Happy tries his luck at golf and launches the ball down to the end of the street, the trees are clearly in autumn colors. However, when you look down the street the trees are green.
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When Happy is first dumped by his girlfriend, he throws his sports bag down in front of the open door. Later in the same scene, the Asian woman opens the door to his apartment, which should have been open already. It is not possible for it to have shut due to his bag being in the way.
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At the beginning of the Tour, Happy is gloating about his newly discovered golf skills to Shooter. There is one medium close-up of the two and it is raining in the background. The shots preceding and following this MCU do not have any rain.
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When the VW turns the corner on the grass you can tell that they have done that shot a number of times as there is already tire tracks on the grass.
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When Happy is asking his caddy for advice on a putt, he says "slightly downhill?" The caddy, clearly bending over to view the putt replies, "and slanting left." Happy then says, "it only seems that way because you only have one shoe on." The next shot is of the caddy standing up with his left shoe off. The next shot he is bending over again and says, "oh yeah."
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The hockey teams on the ice when the player takes the slap shot that killed Happy's dad are totally different than the two teams shown earlier in the fight. In fact, it is actually one team, in practice jerseys, at a practice rink. You can tell because there is no crowd in the background for the shot, but other shots reveal they are in a fully encircled arena.
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When Happy is in the batting cages, Chubbs pulls the plug for the pitching machine causing it to stop. The cable is visibly unplugged in the next scene but when the young boy enters the cage the machine still works.
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Errors in geography 

The flag in the background in the office at the Portland, Oregon, Open is a Washington State flag.
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At the Michelob Open, a sign for the Visa Everglades Open is visible in the background.
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Factual errors 

Fans are not allowed on the course during a PGA event. This fact is ignored frequently in the movie.
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When Happy is in the "cabbage" we can easily assume he takes strokes 2,3,4,5,6 and 7, which goes in the water. As the ball moves a little each time, all the strokes would count. A 1 shot penalty would also apply, meaning his next shot would be 8. Even if he holed out his 8th shot his score would have dropped much more than indicated in the movie. His score only went from -5 to -1, a loss of only 1 stroke. Unless the hole was a par 7 (of which there are none on the PGA Tour), this is inaccurate.
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You can not grip a club below the grip. Happy putts with one hand on the shaft every time.
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In the opening scene where Happy is at a hockey game with his day watching their favorite player Terry O'Reilly, the close up shows that the players are on roller blades, not ice skates. O'Reilly played in the NHL for the Bruins, and never played roller hockey.
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Incorrectly regarded as goofs 

After Bob Barker throws Happy in the water, they roll down the hill together. When they reach the bottom, both are completely dry. It may seem like they are both dry. But Happy is still wet when Bob Barker is punching him. The back of Bob's pants are wet, as you can tell when he walks away.
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Revealing mistakes 

After Happy knocks Chubbs' wooden hand off with the hockey stick, Chubbs' right hand is clearly visible.
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The alligator sliding into the water after Happy grabs for Chubbs' hand is obviously stock footage.
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Obvious knee pads on the IRS agent Happy throws through the door of his grandmother's house.
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When Happy putts the ball too far and it rolls back into the hole, the groove carved in the ground to direct the ball is clearly visible.
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When the movers are at Grandma's House, they bet that Happy can't hit the ball. After he swings, the ball can be seen being pulled back through his legs, under the grass. This is visible throughout the movie in several spots.
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When Bob Barker and Happy Gilmore are rolling down the hill, at the very end of the shot, you can see Bob Barker's stuntman's face.
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After Shooter McGavin invites Happy to the gold green at 9pm as a gag, he quickly looks at the camera for a fraction of a second when he turns toward it.
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When Mr. Larson is trying to intimidate Shooter, he pulls one of his clubs out of Shooter's bag and bends it considerably into a "U" shape. The shaft in the club is made of steel, so if he were to bend it just slightly, it would snap in two. The same argument could be made if the shaft were graphite.
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During the opening scene for the tour championship. The Volkswagen bug can be seen against the tower. That scene is not until the end of the movie.
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Spoilers 

The goofs below may give away important plot points.

Audio/visual unsynchronised 

When Shooter takes Happy's jacket after Happy's last putt, we see Shooter running down a slanted section of ground, with people chasing behind him. However, the noises of fans beating up Shooter start even before his left hand is out of the shot, and nobody is close enough to him to be hitting him.
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Continuity 

At the end of the movie when the TV tower is falling, the position of the people falling off changes between shots.
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Continuity 

On the final day of the players championship Shooter tees off and makes a divot. In the next frame shooter turns too talk to Happy and the divot is gone.
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Continuity 

On the first day of the tour championship you can see the VW beetle crashed into the TV tower, this does not happy until the third day of play.
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Factual errors 

During the final round of the Tour Championship, Shooter is forced to hit the ball off of Mr. Larson's foot. Even if a spectator let a ball come to rest on their foot, PGA rules would clearly give Shooter a free drop.
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Factual errors 

During the final round of the Tour Championship, Happy is forced to hit the ball, despite the TV tower laying across the green. Even if play were allowed to continue, the tower would either be moved, or Gilmore would get free relief.
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