Tottenham paid Rangers £9m in 2008 and the Scotland international right-back, who later moved on to Real Mallorca and Aston Villa, reluctantly left Ibrox for a fee which swelled the bank balance and set a new club record.
The standard bearer stood for a long time – until another right-back moved in early 2022 and Nathan Patterson followed Hutton’s path to the English Premier League.
Since then though the record has been beaten again – inside six months – and again by a defender as Calvin Bassey joined Ajax in a Rangers record this week.
Hutton’s Tottenham deal was also dwarfed by another EPL transfer this summer, Joe Aribo moving the defender further down the most valuable sales list while Rangers’ bank balance continues to rise.
Here is a look at the updated top ten for 2022 – which no longer includes Duncan Ferguson, Nikica Jelavic or Claudio Reyna’s moves south – but does, of course, still include the Rangers manager.
2. Nathan Patterson
Sold to Everton, January 2022. Fee: £12m rising to £16m Photo: Rob Carr
3. Joe Aribo
Sold to Southampton, July 2022. Fee: £6m rising to £10m Photo: Justin Setterfield
4. Alan Hutton
Sold to Tottenham Hotspur, January 2008 Fee: £9m Photo: SNS Group Aubrey Washington