Page 272 of No-Nonsense Classical Mechanics sketches why paths in phase space can never intersect:
Problem: It seems to me this reasoning only implies that paths can never "strictly" intersect, in the sense that two points in phase space pass through the same point (at $t$), and then split into two distinct paths.
Question: Can't two paths in phase space merge into one single path? It seems to avoid this argument entirely.
Rigor: To make this more rigorous: suppose for sake of argument that two paths "strictly" intersect. Let the first path be $(q_1, p_1)$ and the second path be $(q_2, p_2)$. Suppose at time $t$ there is an intersection: $q_1 = q_2$ and $p_1 = p_2$ (I'm abusing notation here by referring to $q$ and $p$ as both paths and points). Since there is an intersection between two distinct paths, then $dq_1/dt ≠ dq_2/dt$. Yet according to Hamilton's equations: $dq_1/dt = ∂H/∂p_1 = ∂H/p_2 = dq_2/dt$, which is a contradiction. But notice this argument doesn't work when two paths "merge" into one path, since in that case we couldn't say that $dq_1/dt ≠ dq_2/dt$ at the point that the paths merge.
Thus it seems entirely consistent with Hamilton's equations that two paths in phase space could merge into one path.