Upper limb tennis injuries are primarily chronic, resulting from repetitive overuse. We developed a wearable device which simultaneously measures risk factors (grip strength, forearm muscle activity, and vibrational data) associated with elbow tendinopathy development resulting from tennis players’ technique. We tested the device on experienced (n = 18) and recreational (n = 22) tennis players hitting forehand cross-court at both flat and topspin spin levels under realistic playing conditions. Using statistical parametric mapping analysis, our results showed that all players showed a similar level of grip strength at impact, regardless of spin level, and the grip strength at impact did not influence the percentage of impact shock transfer to the wrist and elbow. Experienced players hitting with topspin exhibited the highest ball spin rotation, low-to-high swing path brushing action, and shock transfer to the wrist and elbow compared to the results obtained while hitting the ball flat, or when compared to the results obtained from recreational players. Recreational players exhibited significantly higher extensor activity during most of the follow through phase compared to the experienced players for both spin levels, potentially putting them at greater risk for developing lateral elbow tendinopathy. We successfully demonstrated that wearable technologies can be used to measure risk factors associated with elbow injury development in tennis players under realistic playing conditions.