Single-ISA heterogeneous systems (such as ARM big.LITTLE) are an attractive solution for embedded platforms as they expose performance/energy trade-offs directly to the operating system. Recent works have demonstrated the ability to increase their efficiency by using VLIW cores, supported through Dynamic Binary Translation (DBT) to maintain the illusion of a single-ISA system. However, VLIW cores cannot rival with Outof- Order (OoO) cores when it comes to performance, mainly because they do not use speculative execution. In this work, we study how it is possible to use memory dependency speculation during the DBT process. Our approach enables fine-grained speculation optimizations thanks to a combination of hardware and software. Our results show that our approach leads to a geo-mean speed-up of 10% at the price of a 7% area overhead.