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🤪25 designs · Updated for 2026

Intermediate Silly Pumpkin Stencils

Looking for intermediate silly pumpkin stencils? You're in the right place. Print at 100% scale, tape it to your pumpkin, and poke through the lines with a pin.

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25 intermediate silly pumpkin stencils

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

Intermediate

Split Tooth and Two Sparkles

A giant molar with a split between its two roots gleams at the center, flanked by a four-point sparkle on each side and two small dot accents. The tooth outline is cut through around its lobed crown and twin roots, and the sparkles and dots are pierced as well, making a bright emblem any dentist would love. At medium difficulty, the pinch between the roots is the tightest cut, so saw into that notch from both sides and go slow.

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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

Crossed Eyes and Buck Teeth

Huge crossed googly eyes sit under raised brow slots while a gaping oval mouth shows off two goofy buck teeth, with freckle dots on each cheek. The eyes, brows, mouth, and dots are all pierced through, and the dark pupils and teeth are rind left attached inside the openings. Those attached pupils and teeth are the tricky bit; cut around them slowly and leave their connecting bridges generously wide.

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Intermediate

Teardrop Eyes and Three Stars

Two enormous teardrop eyes dominate this quirky alien mug, floating above a tiny triangle nose and a crooked grin made of separate oval mouth slots, with three little stars sprinkled around the face. Every eye, slot, and star is cut through, giving the pumpkin a goofy otherworldly stare. At medium difficulty, carve the huge eyes last since removing that much wall weakens the face, and keep the small oval grin slots evenly spaced.

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Intermediate

Raised Brows and Four Tears

A theatrically miserable pumpkin with worried brows arched high, drooping oval eyes, four teardrops sliding down the cheeks, and a deep downturned frown showing a hint of teeth. Every brow, eye, tear, and the big frown is cut through so the whole sob story glows. A medium carve that lands the joke best when the tears line up; cut the small teardrops first, then the eyes, saving the wide mouth for the end.

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Intermediate

Wide Eyes and Eight Cheek Dots

Raised eyebrow slivers arc over two huge oval eyes, while a big O shaped mouth gasps below and four round dots freckle each cheek. All the openings are simple pierced shapes, but their sheer number bumps this into medium territory. Drill or core the eight cheek dots first while the wall is still strong, then cut the large eyes and mouth so the face keeps its comic shocked stare.

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Intermediate

Unequal Eyes and Crooked Teeth

This lovably lopsided face pairs one round eye with one droopy crescent eye, a triangle nose, and a huge crooked grin full of uneven square teeth, plus a pair of dot dimples on each cheek. The eyes, nose, mouth, and dots are pierced while the mismatched tooth bars stay attached. It suits odd-shaped pumpkins perfectly; cut the tooth gaps in random sizes and the wonkier it looks, the better.

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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 Rounded Teeth

Three round eyes line up across the brow of this cheerful monster, above a wide grinning mouth with four rounded teeth hanging from the top lip and a small diamond accent cut on each cheek. The eyes, diamonds, and mouth are cut through, with the teeth left attached to the upper mouth edge. At medium difficulty, the main care point is those hanging teeth: cut around each one gently, and try it on a green or warty pumpkin for extra monster energy.

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