We go back nine years to find this latest memorable match between the two sides who will meet in Carabao Cup action at Deepdale on Tuesday night.
And it was a game where North End had the last hurrah, thanks to Billy Jones; here's the report from a four-goal thriller...
Billy Jones scored a last-minute header to snatch a point for Preston North End at Deepdale.
Middlesbrough dominated the opening half and took the lead when Gary O'Neil, who had already been denied by Andy Lonergan, scored with a free-kick.
Paul Parry levelled with a neat finish from a tight angle after Brad Jones has parried Jon Parkin's header, but Adam Johnson restored Boro's lead with a low shot into the bottom corner and Rhys Williams hit the post but Jones converted a Ross Wallace free-kick.
The match was Colin Cooper's only game in charge of Boro before the club made a permanent appointment as successor to Gareth Southgate. On the evidence of the first-half, Boro should have taken all three points from the encounter.
The visiting team, encouraged by considerable away support, created a series of decent openings, but the Lilywhites rallied after the break and their perseverance was rewarded with their late equaliser - although the draw means that North End dropped out of the top six.
After the game PNE manager Alan Irvine said: "I'm not over-happy. We have got a point, but I look for more than just a result. There are a lot of things we will need to take out of that game and improve upon.
"We were poor in the first half. I was praying for half-time to come to address some of the issues that needed addressing.
"I thought we got the response almost from the kick-off in the second half. We then started to stretch the game out a bit better than we had in the first half. They deserve enormous credit for keeping going. It's a fantastic quality to have."
Whilst Boro caretaker manager Colin Cooper added: "Unfortunately it comes a bit too much of a coincidence when you concede two to three late goals. We should be sitting fairly close to the top of the table with the points that have gone begging.
"Hopefully we will learn and not make mistakes in a game that we should have won comfortably."
PNE line-up: Lonergan, Collins, Chilvers, Jones, Nolan, Shumulikoski (Chaplow, 57), Carter (Brown, 77), Parry, Wallace, Parkin, Mellor (Elliott, 90). Subs not used: Henderson, Hart, Mawene, Sedgwick.
Middlesbrough line-up: Brad Jones, Hoyte, St. Ledger, Bennett, Wheater, Digard, O'Neil, A Johnson, Williams, Lita, Emnes (Franks, 90). Subs not used: Coyne, Pogatetz, Grounds, McMahon, Yeates, Arca.
Referee: Mr Andy Woolmer