What You're Actually Looking For
Most Halloween math worksheets you'll find online are basic addition and subtraction problems wrapped in spooky clip art. That's it. The concept isn't complicated, but finding one that actually works for your child takes a bit of effort because a lot of the free stuff out there is poorly made. I spent last October trying to print worksheets for a second grader who could do single-digit addition fine but completely stalled on subtraction with regrouping when the numbers got above ten. I went through about forty different resources before finding something that wasn't either too babyish or way above grade level.The trick is filtering for the actual math skill first and treating the Halloween theme as a secondary feature. Too many people start with the theme and end up with worksheets where the problems are trivial—"2 + 2 = ?" with a pumpkin next to it—while claiming they're appropriate for third grade. That wastes time and undermines whatever momentum the kid has built up. Here's what I ended up doing when I couldn't find the right mix: I took a plain printable sheet of addition and subtraction problems from a teacher resource site and swapped out the clip art myself. I used free Halloween graphics from Openclipart and pasted them in next to the equations using a basic word processor. It took me about twenty minutes and the result was better than anything I found pre-made. My kid actually preferred it because it felt less like a workbook someone else made and more like something real. When you're looking at a worksheet, check the answer key first. I've seen too many free resources where the answer key doesn't match the problems. It happens constantly. One site I checked had eight subtraction problems and the key had answers that matched a completely different set of problems. Wasted a whole morning on that one.
What makes a worksheet actually useful The math facts need to be at the right difficulty level for the student. If they're already finishing the problems in under five minutes without thinking, the worksheet is too easy regardless of how cute the jack-o-lanterns are. If they're spending ten minutes on each problem and getting frustrated, it's too hard. There's a middle zone where the work takes about eight to twelve minutes and they get about eighty percent right on the first try. That's where learning happens.Another thing most people miss: the layout matters. Worksheets where problems are cramped together with no space between rows cause kids to skip lines or add numbers from adjacent problems by accident. I always look for at least an inch of white space between each equation. It's a small thing but it cuts down on careless errors significantly.
I also recommend having the student solve the problems in order rather than letting them pick and choose. Kids will naturally gravitate toward the problems they find easy and skip the ones they struggle with. That creates a false sense of mastery. They finish the page feeling good and then get blindsided on a quiz by a problem type they avoided.Print two copies of whatever you use. Let the first copy be the working version where they show their work. If the answer is wrong, they can see where they went off track. The second copy is for a clean retake after reviewing the mistakes. This doubles your practice in the same amount of time without needing to find new material.
Get the Full Details

If you want something specifically for subtraction with regrouping around the holidays, search for "Halloween subtraction with regrouping worksheets" and sort by recent. A lot of older worksheets have typos or outdated numbers that don't make sense. Something posted in the last two years is more likely to be accurate.
The main limitation with these themed worksheets is that they don't adapt to the individual student. Once you've worked through a set, there's no mechanism to generate harder or easier problems on the fly. If your kid is ahead, you'll need to supplement with something like a simple spreadsheet where you can vary the number ranges. If they're behind, you'll need to pull out worksheets with fewer problems and smaller numbers even if they don't have a Halloween theme.I keep a folder of plain addition and subtraction sheets at different difficulty levels ready to go whenever the themed ones aren't quite hitting the mark. The theme is fun but it's not going to fix a gap in understanding. That takes repetition at the right level.