In this study, a machine learning-based method to assess and predict the cracking degree (CD) on wood fiber bundles (WFB) was developed, which is crucial for enhancing the quality control and refining the production process of wood scrimber (WS). By roller-cracking poplar wood one to three times, three distinct CD levels were established, and 361 WFB specimens were analyzed, using their water absorption rate (WAR) as the foundation for CD prediction. Through crack image analysis, four key quantitative parameters were identified—cracking density, coherence degree, crack count, and average width—and this study found through discriminant analysis that the discrimination accuracy on the CD levels by cracking density or coherence degree over 90%, emphasizing their significance in evaluation. Cluster analysis grouped the specimens into three clusters based on four key quantitative parameters, aligning with the CD levels. This study developed specialized prediction models for each CD level, integrating principal component analysis for dimensionality reduction with polynomial fitting, achieving mean squared error (MSE) of 0.0132, 0.0498, and 0.0204 for levels 1, 2, and 3, respectively. An integrated model, with an accuracy of 94.3% and predictions within a 20% error margin, was created, demonstrating the effectiveness of using surface crack image features to predict WAR of WFB. This research establishes a methodological framework for assessing CDs on WFB, contributing to enhancing WS product quality and helping to better understand wood cracking and water absorption mechanisms.