Joe Royle promised one of his numerous "watersheds" after the ignominious removal of Everton from the 1996 FA Cup campaign at the hands of Port Vale. Royle's wrath was directed at Matthew Jackson, who was destined never to play again for Everton. This opened up a chance for Jon O'Connor to appear in the first team, making a good impression in his debut at Old Trafford. He was excellent in his next game against Nottingham Forest at Goodison Park. Another good performance at Middlesbrough included setting up one of the goals. Despite earning accolades all round from the fans, it appears he was not good enough for Royle, who had earlier engaged the services of Marc Hottiger. A work permit finally came through for the Swiss International, and Jon went back to the Pontin's League.
But Jon then discovered in July 1996 that he needed a hernia operation. After a groin strain, he finally plays in reserves by November 1996, but that is short-lived as the hernia problem requires a second operation. In the spring of 1997, when the hernia seemed finally conquered, Jon picked up a thigh strain requiring at least 6 weeks rest. These niggling injury problems eventually kept him on the sidelines for the entire 1996-97 season, although he did sign a new 3-year contract with the club.
In the pre-season friendlies during the summer of 1997, O'Connor was one of the bright spots, linking very well with new boy John Oster down the right wing. But this must have occurred on the far side of the field from Howard Kendall, who went out and bought Tony Thomas to increase competition in this key slot – the second time Jon's skills had been spurned in this way. This became yet another setback in Jon's stop-start career, as his solid performances in the reserves continued to be ignored by Howard Kendall, who then went out and bought John O'Kane from Manchester United.
The inevitable parting of the ways came in February 1998 as Jon joined Graham Stuart and Earl Barrett at Sheffield United – a real pity because, with the right grooming, he could have become an excellent player for Everton.
Cup Statistics include all other non-league senior matches, as counted by Everton FC in the Matchday Programme
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