I can't recall purchasing any weird items but I remember two things that I purchased which saved/earned my friends and I a little bit of money.
First in the early/mid 1990 my girlfriend and I went on holiday for a week to the seaside. The local pub that we went in had Guinness so we bought two pints and with the pints came two scratchcards. If you scratched the correct boxes you won a free pint of Guinness. We quickly worked out that if you held the scratchcard up to any light source the correct boxes were obvious. The bar staff compounded this error by giving away another scratchcard with the free pint that you had won. We probably drank 70-80 pints of Guinness that week and only paid for the first two.
The next one was in the late 1990s my friends and I were out and spotted a pub quiz advertised. We went in and got a table about 30 mins before the advertised starting time. When the quiz host came to the bar and announced the quiz was starting buy your sheets, I went up and paid £1 and got a sheet with numbers 1-30.
When I got back to the table I gave it to my mate's girlfriend as she had the neatest writing and was the least drunk. Only then did we realise that he had printed the answers on the back. We noticed the host frantically searching for his answer sheet just before the quiz started but he must have thought he had left it at home and went with trying to remember the answers.
We did think about been honest but realised we were never going to be allowed to enter even if we handed it back. The team we beat into second apparently won almost every week and consisted of about 5-6 middle/old aged couples who were blatantly cheating by asking the young lads playing darts and pool to fill in any gaps in their knowledge.