Tested on 20190707-master-g1e723934a1 and 20200509-master-g61e1a45100, though bug probably present since the dawn of OpenTTD
When you have more than 2,147,483,647 road pieces, then the infrastructure count should just keep on going up with no overflow.
When you have more than 2,147,483,647 road pieces, the infrastructure count in the company window does not overflow right away, but in the infrastructure detail window, it does. Additionally, without NewGRFs and with default settings, the amount you are paying for road infrastructure maintenance yearly (proportional to approximately [count]^1.5) flips from positive £32.654 trillion to negative £32.654 trillion.
EDIT: At 4,294,967,296 road pieces (and all multiples thereof), the infrastructure count in the company window DOES overflow, going back to 0. In both cases, the cause is that all infrastructure counts are stored as 32-bit integers (uint32 in the company window, signed int32 for infrastructure details window and infrastructure cost calculation).
Give yourself £1 quadrillion (1,000,000,000,000,000) on both companies (company 0 and 1). NOTE: You will have to use an external program such as Cheat Engine or AutoHotKey to accomplish this, as the change money cheat would take several tens of millions of clicks to get the required amount of money.
Make sure to turn on the tunnel cross cheat. If you don't, the next step will take up to several real-life days to complete, depending on your system (time spent checking against existing tunnels).
Unpause the game and wait approximately 2.5 ingame years, making sure to save every month or 3 months.
Watch as the infrastructure counter overflows.
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