The cycling fanatic completed the gruelling 6 kilometre climb of Monte Zoncolan, arguably the toughest climb in professional cycling and frequently used in the Giro d'Italia.
"The ascent to the summit is much harder than even the toughest mountains at the Tour de France," Guidolin said.
At 52 years-of-age, Guidolin completed the ascent in 56 minutes and five seconds. By comparison, Australian cyclist Michael Rogers complted the ascent last year with a time of 43 minutes 55 seconds - on his way to winning a stage on the 2015 Giro d'Italia.
"The first time I confronted the side of Ovaro was deadly - the steep narrow roads, poor light. I had to get off the bike and walk for 500 metres. I have no idea how I managed to finish," Guidolin said.
Eight years on, the Italian now faces a daunting climb up the Premier League table as Swansea languish dangerously close to the relegation zone - with the 1-0 win over Watford lifting them to 17th as Guidolin looked on from the stands.
Credited with transforming Alexis anchez into the creative forward at Udinese, Guidolin boasts a wealth of experience, managing 15 clubs in 28 years and the Welsh side will need every bit of it to revive their season.