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And before that they used to be more expensive to upgrade, following the exact same pricing policy as now. And (2), I bet you said to your mate something along the lines of "You can have the ticket for free, just cover the upgrade charge" so he got it cheaper anyway.

No.

At the ticket office windows right up until kickoff.

When we started at the Amex this is exactly how the ticket upgrades worked. Then, when the ticketing system was changed it hot cheaper ad the cost was based on the pro-rata-ed season ticket price. We're now back to what we originally had.