Bundles apply per "direction" - they should show up clearly associated one with or more segments linked by what United considers to be transfers. The Club access is valid at all points in that direction of travel (origin, connection, and destination). So you should see a club bundle for outbound (valid at CLE, DEN, and SFO) and for inbound (SFO, ORD, CLE). If you're doing a same-day turn it might be complicated.

That's what I usually see - not sure if you're saying you only see one.