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🎃22 designs · Updated for 2026

Intermediate Toothy Grin Pumpkin Stencils

We rounded up the best intermediate toothy grin pumpkin stencils so you can stop scrolling and start carving. Each design comes with a clean PDF you can print at letter size.

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22 intermediate toothy grin pumpkin stencils

Beginner or pro, there's something on this page for you.

Intermediate

Wink and Five Rounded Gaps

One eye is a jaunty upswept crescent wink while the other stays a wide triangle, set over a small diamond nose and a lopsided grin broken into five rounded gaps by chunky teeth. The eyes, nose, and mouth gaps are cut through, leaving the tooth shapes as attached skin between them. A medium carver should cut the five mouth gaps individually rather than one big mouth, which keeps every tooth solidly connected and the crooked smile intact.

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Intermediate

Winking Seven-Tooth Grin

A goofy winking jack-o'-lantern with one wide round eye, one squinting wink, a triangle nose, and an enormous grin broken up by a jumble of square and pointed teeth along both lips. Every feature is cut clean through so the mismatched expression beams from the whole face. At medium difficulty the mouth is the main event; cut the grin outline first, then shape each tooth individually, alternating sides so the lip strips stay supported.

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Intermediate

Cyclops Eye and Five Teeth

A goofy cyclops with one giant round eye under a curly brow, a small triangle nose, freckle dots on each cheek, and a huge laughing mouth with five stubby teeth. The features are cut through, and the pupil stays in place as an attached tab hanging inside the enormous eye. That pupil bridge is the medium-level test; cut both sides of the tab before freeing the rest of the eye circle.

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Intermediate

Wink and Barred Square Grin

One huge round eye stares while the other squeezes into a curled wink above a giant open grin packed with blocky square teeth, and freckle dots sprinkle each cheek. The eyes, mouth, and freckles all cut through the wall, with skin bridges left in place to form the teeth. Cut the mouth's outer outline first, then remove the gaps between teeth one at a time so each block stays anchored.

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Intermediate

Oval Eyes and Eight Cheek Dots

Big oval eyes sit under arched brows above a round button nose and a broad smile showing four blunt square teeth, with four freckle dots sprinkled on each cheek. The eyes, brows, nose, mouth, and dots are pierced through while the tooth bridges stay connected. Poke the eight small cheek dots first, then cut the large features, leaving the tooth bars until the end so they keep support.

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Intermediate

Curved Horns and Diamond Chin

A devilish face with two curved horns sprouting from the brow, narrow slanted eyes glaring beneath them, a wide grin studded with square teeth, and a diamond goatee stamped under the chin. Every piece is cut through so the whole sinister face burns bright. A medium carve with lots of payoff; cut the horn tips slowly since their curved points are the thinnest cuts, and finish with the easy diamond chin.

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Intermediate

Barred Eyes and Cheek Tears

A goofy clown face with big round eyes crossed by horizontal rind bars, teardrop shapes dangling from each cheek, a button nose, and a huge grin with three chunky teeth. The eyes, tears, nose, and mouth are all cut through, while the eye bars and teeth stay as attached rind bridges. Those bars make it a medium carve: cut each eye as an upper and lower opening on either side of the bar, supporting the bridge with a finger as you finish the strokes.

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Intermediate

Three Eyes and Four Teeth

Three round eyes of different sizes line up above a small rectangular nose and a wavy grin broken by four square teeth, giving this mutant jack-o'-lantern a delightfully goofy personality. The eyes, nose, and mouth are all cut through, with the teeth left as tabs, and tiny freckle dots may be etched shallow on the cheeks. A medium carve mainly for tooth care; cut into the grin from between the teeth so each square tab keeps its corners.

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Intermediate

Almond Eyes and Seven Teeth

A wide, low jack-o'-lantern face with sly almond-shaped eyes, a small triangle nose, and a long jagged mouth packed with alternating square teeth top and bottom. Everything is pierced through, and the horizontal layout suits squat, wide pumpkins. At medium difficulty the tooth row is the main work; cut the mouth's outer outline first, then remove the gaps between teeth one at a time so each block keeps support while you work.

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Intermediate

Tall Smile and Six Cheek Dots

A tall pumpkin design with arched happy eyes, an oval nose, three dot freckles on each cheek, and a huge open smile with four little teeth hanging from the top lip. Every shape is cut through, and the six small cheek dots add a sprinkle of glowing freckles around the grin. Punch the freckle dots with an apple corer or drill bit before opening the big mouth.

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Intermediate

Angled Eyes and Seven Fangs

Two sharply slanted triangle eyes glare above a wide jagged mouth lined with seven pointed fangs, giving this face a classic menacing snarl. Every element is cut fully through, and the zigzag mouth does most of the work, so accuracy there pays off. Cut each tooth as two separate straight strokes meeting at the point instead of dragging the saw around the corner, and the grin stays razor sharp.

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Intermediate

Six-Slot Grin and Cheek Slits

Two arched, angry eyes glower above a huge crescent grin broken into a row of glowing tooth slots, with small slits flaring at each cheek. All the features are pierced through the wall, and the strips of rind left between the tooth openings become the dark teeth of the smile. Cut the mouth slots from the center outward and leave the narrow rind bridges at full thickness so the grin holds its shape.

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