diff --git a/packages/tldraw/src/lib/tools/SelectTool/childStates/Brushing.ts b/packages/tldraw/src/lib/tools/SelectTool/childStates/Brushing.ts
index 28e094c6efca..9cec0a067c4c 100644
--- a/packages/tldraw/src/lib/tools/SelectTool/childStates/Brushing.ts
+++ b/packages/tldraw/src/lib/tools/SelectTool/childStates/Brushing.ts
@@ -24,6 +24,9 @@ export class Brushing extends StateNode {
 	excludedShapeIds = new Set<TLShapeId>()
 	isWrapMode = false
 
+	selectionOrder = new Map<TLShapeId, number>()
+	private orderCounter = 0
+
 	viewportDidChange = false
 	cleanupViewportChangeReactor() {
 		void null
@@ -62,6 +65,8 @@ export class Brushing extends StateNode {
 
 		this.info = info
 		this.initialSelectedShapeIds = editor.getSelectedShapeIds().slice()
+		this.selectionOrder.clear()
+		this.orderCounter = 0
 		this.hitTestShapes()
 		isInitialCheck = false
 	}
@@ -166,10 +171,7 @@ export class Brushing extends StateNode {
 				editor.updateInstanceState({ brush: { ...brush.toJson() } })
 			}
 
-			const current = editor.getSelectedShapeIds()
-			if (current.length !== results.size || current.some((id) => !results.has(id))) {
-				editor.setSelectedShapes(Array.from(results))
-			}
+			this.setOrderedSelectedShapes(results)
 			return
 		}
 
@@ -225,9 +227,30 @@ export class Brushing extends StateNode {
 			editor.updateInstanceState({ brush: { ...brush.toJson() } })
 		}
 
-		const current = editor.getSelectedShapeIds()
-		if (current.length !== results.size || current.some((id) => !results.has(id))) {
-			editor.setSelectedShapes(Array.from(results))
+		this.setOrderedSelectedShapes(results)
+	}
+
+	private setOrderedSelectedShapes(results: Set<TLShapeId>) {
+		// Track entry order for newly selected shapes
+		for (const id of results) {
+			if (!this.selectionOrder.has(id)) {
+				this.selectionOrder.set(id, this.orderCounter++)
+			}
+		}
+		// Remove shapes that left the selection
+		for (const id of this.selectionOrder.keys()) {
+			if (!results.has(id)) {
+				this.selectionOrder.delete(id)
+			}
+		}
+
+		const ordered = Array.from(results).sort(
+			(a, b) => (this.selectionOrder.get(a) ?? 0) - (this.selectionOrder.get(b) ?? 0)
+		)
+
+		const current = this.editor.getSelectedShapeIds()
+		if (current.length !== ordered.length || current.some((id, i) => id !== ordered[i])) {
+			this.editor.setSelectedShapes(ordered)
 		}
 	}