In make-to-order manufacturing workshops, accurate prediction value of production progress (PP) is a significant reference index for dynamic optimisation of production process and on-time delivery of production orders. The implementation of big data and Industrial Internet of Things (IIoT) in manufacturing workshops makes it possible to obtain large amounts of production data which can affect PP. However, the particularities of massive historical order data are not fully excavated and the amount of target order data is insufficient to support the training of high-precision prediction model, which will result in bad training approximation and generalisation. To overcome these shortcomings, a PP prediction approach consisting of two models with transfer learning (TL) is proposed. TL can avoid the training of PP prediction model from scratch every time. Consequently, computational efficiency can be greatly improved. A convolutional neural network (CNN) model with TL is devised to excavate the comprehensive features from historical and current orders. Additionally, a long short-term memory network (LSTM) model with TL is constructed to fit the nonlinear relation of the features provided by CNN-TL model for PP prediction. In order to validate the performance of the proposed PP prediction approach, comparative experiments of eight algorithms are conducted in an IIoT-enabled manufacturing workshop.