WeierstrasssubstitutionA Weierstrass substitution \[Psi]ψ -> 2 ArcTan[u\[Psi]]ArcTan[uψ]
is the way to solve these equations:
eqn = {-a r Cos[\[Phi]]Cos[ϕ] == R Cos[\[Psi]]Cos[ψ],
r Sin[\[Phi]]Sin[ϕ] == R Sin[\[Psi]]Sin[ψ]} /. \[Psi]ψ -> 2 ArcTan[u\[Psi]]ArcTan[uψ] //TrigExpand
solu\[Psi]soluψ = Solve[eqn, {R, u\[Psi]uψ}] ;];
sol\[Psi]solψ = solu\[Psi]soluψ /. u\[Psi]uψ -> Tan[\[Psi]Tan[ψ/2]
(*{{R -> -r Sqrt[a^2 Cos[\[Phi]]^2Cos[ϕ]^2 + Sin[\[Phi]]^2]Sin[ϕ]^2],
Tan[\[Psi]Tan[ψ/2] ->a Cot[\[Phi]]Cot[ϕ] -Csc[\[Phi]]Csc[ϕ] Sqrt[a^2 Cos[\[Phi]]^2Cos[ϕ]^2 +Sin[\[Phi]]^2]+Sin[ϕ]^2]}
,
{R ->r Sqrt[a^2 Cos[\[Phi]]^2Cos[ϕ]^2 + Sin[\[Phi]]^2]Sin[ϕ]^2],
Tan[\[Psi]Tan[ψ/2] ->Csc[\[Phi]]>Csc[ϕ] (a Cos[\[Phi]]Cos[ϕ] + Sqrt[a^2 Cos[\[Phi]]^2Cos[ϕ]^2 +Sin[\[Phi]]^2]+Sin[ϕ]^2])}}*)
Knowing
Tan[x] == (2 Tan[x/2])/(1 - Tan[x/2]^2) // FullSimplify (*True*)
we get
tan\[Psi]tanψ = (2 Tan[ \[Psi]ψ/2])/(1 - Tan[ \[Psi]ψ/2]^2) /. sol\[Psi]solψ// FullSimplify
(* {-(Tan[\[Phi]]Tan[ϕ]/a), -(Tan[\[Phi]]Tan[ϕ]/a)}*)
Hope it helps!