Glasgow Rangers have had plenty of successes and failures in the transfer market over the years as they have unearthed gems but also brought in disappointing flops.
In recent years, the Light Blues have snapped up the likes of Glen Kamara, Ryan Kent, James Tavernier, and Connor Goldson, but have also signed the likes of Cedric Itten, Jack Simpson, and Carlos Pena.
They have also allowed players to leave who have then gone on to achieve greater things in the game, potentially leaving the Gers regretting their decision.
One player the club had a nightmare with was English attacker Martyn Waghorn when they sold him to Ipswich for a reported fee of £1m in 2017.
The Light Blues had signed him from Wigan in the summer of 2015 whilst they were in the second division of Scottish football and he played a major role in their promotion to the Premiership.
In his second campaign in Glasgow, the Englishman produced 16 strikes and nine assists in 41 appearances in all competitions and this meant that he managed 44 goals and 17 assists in 78 matches for Rangers in his first two seasons.
It was reported that the striker was unhappy with his contract situation at Ibrox and was disappointed that they were unwilling to offer him a lucrative new deal during the 2016/17 campaign, which led to his departure to Suffolk at the end of that season.
He ended up spending just one year with the Tractor Boys as he enjoyed a phenomenal season with Ipswich. The attacker scored 16 times and amassed 13 assists in 44 Championship outings for the Blues, which earned him a big-money switch to Derby County.
Waghorn departed East Anglia to sign for the Rams in a deal that was reportedly worth up to a staggering £7.5m. This means that his value rocketed by 650% between the time that he left Rangers and the day that he signed for Derby, after his sensational campaign in the second tier of English football.
The dynamo, who Frank Lampard once hailed for his “incredible” work rate, thrived after leaving Scotland and the Light Blues will surely be regretting their decision not to offer him a sizeable contract extension as he could have fulfilled his potential whilst playing in the Premiership.
Therefore, Rangers had a nightmare with the sale of Waghorn for £1m in 2017 and may wonder how he would have fared if he had stayed at Ibrox for a few more years.