Oliver had the last laugh against his fellow clubman as Melbourne held off a plucky North Melbourne by 30 points at Hobart's Blundstone Arena.
The Demons’ undefeated record remains intact, but Oliver and his teammates were made to work for their round seven victory.
North Melbourne led at quarter and half-time as it searched for its maiden win of the season.
Simpkin was at the front of the charge, with the midfielder gathering 30 disposals and a goal.
Rochester's Shaun Atley chipped in with 15 disposals and five score involvements.
However, Oliver (25 touches, seven clearances, one goal) helped Melbourne run away with the contest in the final quarter.
The result rockets the Dees to the top of the ladder for the first time since 2005.
Mooroopna talent Laitham Vandermeer is set to put his hand up for selection this week.
The Western Bulldogs speedster spent a weekend out of the senior line-up after hurting his back in the round six win over GWS.
Bulldogs’ head of sports medicine Chris Bell said on Monday that the youngster would be training to prove his fitness in the coming days.
“Laitham Vandermeer didn't play at the weekend due to persistent back spasms,” Bell said.
“He's come in really well today and if he fully trains without any issues this week, he will return to availability.”
Vandermeer's Bulldogs will look to bounce back after they suffered their first loss of the campaign to Richmond at the weekend.
Kialla's Alex Keath racked up 18 touches and six spoils, while Seymour's Josh Schache kicked one goal in the loss.
Invergordon export Lachie Ash fronted up against his old Shepparton teammate Jordy Butts on Saturday.
Ash walked away with the chocolates over his 2018 premiership teammate in GWS’ 67-point demolition of Adelaide.
Ash finished the game with 22 disposals.
It was a tough day out for the contingent of products at Port Adelaide and Hawthorn.
Echuca's Ollie Wines (37 disposals, one goal), Katamatite's Tom Clurey (13) and Deniliquin's Todd Marshall were unable to get the Power over the line against Brisbane.
And Mansfield's James Cousins (27 disposals), Shepparton's Jarman Impey (23) and Benalla's Harry Morrison (16) all battled hard for Hawthorn in its 69-point loss to St Kilda.
The David Mundy show continued in Fremantle's loss to West Coast.
The Seymour talent and Dockers veteran was best afield for his side with a 29-disposal, seven-clearance and one-goal performance.
And Tallygaroopna's Steele Sidebottom will be hoping his upcoming milestone match is more memorable than Collingwood's 24-point loss to Gold Coast Suns.
Sidebottom will make his 250th appearance for the Pies this weekend.
Kyabram's Nick Holman registered a whopping 27 pressure acts and 12 disposals in the Suns’ win.
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