His slide down the Wembley touchline as the U’s secured promotion back into the Football League, plus three successive wins over Swindon Town – including a first league double over the Robins for 40 years – are memories that will long be etched in the minds of U’s supporters.
But while both are high on my list, my most defining incident of his reign came on a university training ground in Scotland.
Having just fallen short of making the Conference play-offs in his first six months in charge after a remarkable surge up the table, Wilder was rebuilding his squad in the close season.
I was lucky enough to be with the team as they toured Scotland in the summer of 2009.
Many new faces were getting their first taste of life with Oxford, and how their manager worked.
The players were getting ready, and their manager was right in the middle as banter flew – one player getting grief for a haircut, another for his choice of coloured footwear, and one more for his antics 24 hours earlier.
Boots were tied, and as the players made their way towards the pitch, the mood changed – most notably that of the manager. The fun and games ended and things became serious.
A simple drill was set up, which saw midfielders play one-twos, before releasing a winger who would cross for a striker to make a run and try to beat his defender to score.
The first attempt went badly wrong, so the manager explained again what was expected.
A second try was more successful, although not ending with a goal, but then followed a number of failed routines which saw frustration levels rise.
It all proved too much as United’s boss let out an almighty roar and picked up a nearby football which he promptly volleyed 60 yards away.
“It’s not ******* good enough,” he barked. “It’s ******* simple. Pass, pass, cross, score. You’re professional footballers, so ******* do it right. No excuses.”
The outburst clearly surprised many, but it worked.
The players soon knew the levels that were demanded of them on the pitch and others found out, to their cost, what happened if these standards were not kept.
When Wilder was appointed United manager on a cold Sunday morning in 2008, the club was on its knees.
On the brink of administration and sliding down the Blue Square Premier table, the U’s were in a perilous state both on and off the field.
A points deduction was hanging over them after playing the unregistered Eddie Hutchinson and the future looked grim.
But together with chairman Kelvin Thomas, the fortunes were soon to change.
Wilder installed a new confidence in the players, and with a number of new recruits, the U’s charged up the table.
A final-day defeat at home to Northwich saw United just miss out on the play-offs, but hopes were high that the foundations were in place to win promotion 12 months later.
A flying start to the 2009/10 season saw Wilder’s men surge clear at the top of the table.
Not helped by a host of postponements over Christmas, Stevenage clawed the gap back, and when United hit a poor run of form, Graham Westley’s side took over at the top.
Many feel United’s manager brought in too many new faces at a critical time of the season, causing unrest in the Oxford camp.
But the U’s regrouped, and a good end to the season saw them go into the play-offs on a high.
A 3-1 aggregate win over Rushden took United to Wembley, where goals from Matt Green, James Constable and Alfie Potter saw them beat York 3-1 to return to the Football League in front of more than 33,000 Oxford fans.
Potter’s clinching goal was celebrated by Wilder skidding down the touchline on his rear.
Back in the Football League after a four-year absence, it was a steady first season for United.
After a promising start, a poor run followed which saw Wilder come under pressure from a section of fans shortly after signing a new three-year deal.
However, a shock victory at leaders Chesterfield turned their season around.
Six victories from seven games cemented a mid-table place, which is where they were to stay.
Chris Wilder gestures to Oxford’s fans after his side’s draw at Bristol Rovers in 2012
The 2011/12 season is one no Oxford United fan – or Paolo Di Canio – will forget in a hurry.
The fifth match of the campaign saw the U’s travel to arch rivals Swindon Town, where they had not won for 38 years.
The build-up to the match was dominated by Robins boss Di Canio branding U’s striker James Constable a Swindon fan.
But Constable had the last laugh, scoring twice in a famous 2-1 victory.
The U’s were well-placed after three months of the season, but suffered a run of defeats which derailed their promotion bid.
United accepted a bid from Swindon for Constable in January, but the player turned down the chance to talk to Di Canio.
When the Robins came to town for the rematch in March, Constable was sent off after ten minutes, but the ten-man U’s defied the odds to win 2-0.
It proved one of the rare highlights of a disappointing end to the season, which was blighted by injuries.
United sought to fill the void with a number of loan signings, but their season petered out and they missed out on the play-offs.
Wilder’s time at United changed when his greatest ally, chairman Kelvin Thomas, left the club in July 2012.
The relationship between chairman and manager is the single most important factor in a successful football club and the Thomas-Wilder partnership transformed the club, of that there is no doubt.
It was argued by some fans that their relationship was so strong that Wilder’s job was safe, which was not a good thing.
But when you have a chairman and manager working in unison, success can be achieved.
When that relationship breaks down, there is no return. This was to prove critical 18 months later.
A flying start to the 2012/13 season, with new chairman Ian Lenagan at the helm, saw the U’s in the leading pack, but more injuries hit their bid.
The manager was backed by Lenagan at the end of September, but indifferent form followed as United were always playing catch-up for a play-off place.
Many expected the season to be Wilder’s last, but he was reappointed as manager on a one-year deal in April.
It was a move that seemed to divide United fans, especially with home crowds dwindling – a fact many put down to the manager.
A sensational start to the campaign, the highlight of which was a 4-1 opening-day win at Portsmouth, saw United stake an early claim for promotion.
In a Wembley wonderland. From left: Mickey Lewis, Alan Hodgkinson, Andy Melville, Kelvin Thomas and Chris Wilder
Two months later, with the U’s topping the table, Pompey were looking for a new manager and asked for permission to speak to Wilder.
With Lenagan unwilling to offer his manager a new contract so early in the season, the U’s boss spoke to the south coast side, but did not get the job as Richie Barker was handed the hot-seat.
It was clearly evident that the lack of a long-term deal was unsettling United’s boss as he became linked to several other jobs.
On the pitch though, things were still on track, with United retaining a top-three place until a four-game winless streak saw them drop to seventh.
However, the relationship between Wilder and Lenagan became more and more strained.
The manager wanted job security, the chairman wanted to see if he would bring success. It was a stand-off which could not be resolved.
The farce after Saturday’s 1-0 win over Torquay did not show either party in a good light.
Thankfully, both worked quickly to save face, and the news that Wilder has been handed a three-and-a-half year deal with Northampton shows his stature in the game.
Both parties will now move on with their respective challenges – Wilder battling relegation and Lenagan charged with finding a manager to complete the job at Oxford.