Continuity: After Kevin Costner plays the first round of the US Open when he plays horribly, he and his caddie are seen looking at his score being posted on the scoreboard. The number posted for the 18th hole is a 5. Later on, however, when he is talking to Don Johnson in the bar, and Johnson asks him, "How the hell did you shoot an 83?" he replies, "I missed a 5-foot putt on the last hole for an 82." Considering that the announcers say several times that he hit his second shot on number 18 in the water every single day of the tournament, this is impossible. If he hits it in the water, he takes a penalty shot and now he is hitting his fourth shot onto the green, putting for a 5. If he then, as he says, misses the 5 foot putt, he must make a 6 on the hole. I've watched it a thousand times, it just isn't possible.

Continuity: When Earl is Roy's caddy, he stops at the first hole, leans over the golf bag exhausted saying that he wished Romeo was there. The camera angle changes and he is now standing straight up and not breathing hard.

Continuity: After Dave takes his first shot on the final hole, he is seen walking and you can see that his glove is tucked in his back pocket. The camera angle changes to a front view and you see him taking off his glove and tucking it in his back pocket again.

Continuity: Right after the spotter points out to Roy where his ball is in the woods, not only does the spotter disappear, but Roy is seen moving a large leaf that was not even near the ball in the first shot of the scene.

Continuity: After the doctor catches Roy wearing all the golf equipment, they are outside talking and his hair keeps changing from being tucked under his hat to sticking out from under the hat.

Continuity: Nearing the end of the movie, a larger set golfer approaches Molly and asks for a card or two. He has his sunglasses on his head, if you look at his hair, in the first shot its swept down to the side. In the next shot a portion is hanging between the glasses against his forehead. In the following shot as he walks away, his hair is back to sweeping to the side.

Continuity: In the scene where Costner is playing Johnson in the final round, we see both of them lining up their putts. Costner is swinging the grip of the putter from side to side in front of his face. When we see him through Rene Russo's periscope, he is not moving the club at all. The shot cuts back to Costner, and he is swinging the club again.

Continuity: The first lesson Molly has with Roy, it's already dusk, and when they go outside, it's dark. At the end of the lesson, Roy says "Same Time Next Week?" and Mollie says "Okay."  But then in the next lesson Mollie complains that he is late.   But when he does show up for that late lesson, it appears to be in the late afternoon, not even close to dusk.

Continuity: During the first competition when Roy is caddying for David Sims we see Roy offer David the 3 Wood. When David refuses they have a discussion. Watch as you see Roy holding the club in his left hand lower the club down holding it in his hand. Right after the discussion we see Roy then once again pull the 3 Wood from the bag and again offer it to David.

Continuity: As Roy is destroying his clubs during their qualifying rounds, Romeo's stance with the golf bag is different each time the camera pans back to him throughout the scene.

Factual error: During Dave Simms' tournament, Romeo is seen caddying for Craig Stadler. Craig is a world-famous fantastic tour professional and would have his own, regular caddy. Besides, only Tin Cup was offered a caddying job - not Romeo.

Plot hole: Near the start of the film, Molly answers Roy's riddle. But she wasn't there when he asked it, so how does she know the answer?

Continuity: During the scene where Roy is caddying for Dave Simms, Phil Mickelson hits a shot to the green. Roy says, "He's on the green - in good shape too". However, when Roy's ball lands on the green, Phil's ball is nowhere to be seen.

Plot hole: In the scene where Roy takes his ball out of the hole, at the last round of the US Open, the crowd are going wild etc. Dave, who has a chance to win the competition, doesn't finish off his round.

Continuity: When Rene Russo is talking on the phone in her office you see in the alternating shots of her head - her hair is in front of the cord then behind it as the shot changes. Her hair alternates with the shots 5 or 6 times.