A disastrous April had seen Mel Machin's men blow their chances of automatic promotion, with one win in seven also casting doubt over a debut appearance in the play-offs.
The slide had coincided with the transfer deadline day sale of key defender Jamie Vincent to Huddersfield, a not unfamiliar scenario for Cherries followers to stomach.
However, after James Hayter had answered their May Day call by scoring during a vital 1-0 triumph at York, the stage was set.
Victory over Wrexham at Dean Court would have guaranteed Cherries a play-off place, irrespective of results elsewhere.
As it transpired, the occasion was all too much for Cherries, with expectation and anticipation replaced by despondency and despair as the Welshmen held out for a dour 0-0 draw.
For goalscoring midfielder Robinson, one of three Cherries players named in the divisional team of the season, a second successive play-off near-miss proved pivotal.
The realisation hit me that day, recalled Robinson. I knew that if I wanted to play in the Championship or higher, I would probably have to leave. I thought I was capable of doing that and it was just unfortunate that I never got to do it with Bournemouth.
Robinson, who also had an international career with Northern Ireland to consider, spent a further year with Cherries before joining Preston for £375,000.
A hero of their memorable Great Escape in 1995, the effervescent Ulsterman moved on after notching 60 goals in 286 games for the club. Now living near Belfast and working for the Irish FA, he remains one of Cherries' all-time leading goalscorers and appearance-makers.
We were geared up for promotion, both in 1998 and 1999, said Robinson, a highly-decorated coach who holds the prestigious UEFA pro-licence. Bar the stadium, we had everything in place. We should have at least made the play-offs. It was a major disappointment.
Mel had assembled a young squad from nothing and we played with no fear.
We had Mark Stein scoring goals for fun and he was a calming influence. Maybe we needed a few more old heads to see us over the line.
We lacked a bit of consistency but I still feel we under-achieved. The players we had were every bit as good individually as the ones we had at Preston and they romped that league in 2000.
Cherries' ongoing financial difficulties saw several members of Machin's squad eventually leave the club, among them Ian Cox, Richard Hughes and Eddie Howe.
Robinson added: We knew players would go if we didn't get promotion. Bournemouth had always been a selling club and that was always going to be a problem.
I can't speak about the club's finances now but I thought they were turning a corner.
Eddie Howe certainly lifted the profile of the club while he was manager and Lee Bradbury and Steve Fletcher are continuing the good work.
I know it is easier said than done in the current climate, but they should be trying to keep their better players to give the club a chance of going where it deserves to be. That would give the current management a chance to build on what Eddie started.
Ambitious players will always be looking to better themselves and Bournemouth will only be able to convince them to stay if they get into the Championship. I would love to see that happen. I still consider Bournemouth as my club and would love to see them progress.