Major product of the following reaction is:

Here are some examples from Jerry March, which clearly says that the addition of HX across the carbon double bond can give different results based on the reaction conditions and the choice of solvent. The stereochemistry will be different for cyclohexene and slightly different for cyclopentene because in cyclopentene, or you can say the cyclopentene, the bonds have greater eclipsing interactions compared to cyclohexane. That also affects the energy of the transition state and how the attacking reagent will approach the ring.

More clarity is offered by Carey & Sundberg (P478): The stereochemistry of addition of hydrogen halides to unconjugated alkenes is usually anti. This is true for addition of HBr to 1,2-dimethylcyclohexene, cyclohexene, 1,2 dimethylcyclopentene, cyclopentene, Z- and E-2-butene, 2 and 3-hexene, among others.

Anti stereochemistry is also dominant for addition of hydrogen chloride to 1,2-dimethylcyclohexene and 1-methylcyclopentene. Temperature and solvent can modify the stereochemistry, however. For example, although the addition of HCl to 1,2-dimethylcyclohexene is anti near room temperature, syn addition dominates at −78$^oC$