Boro trio Grant Leadbitter, George Friend and Ben Gibson will record major personal milestones when they next pull on a shirt for the Teessiders.
Club captain Leadbitter has shared the armband with Friend and Gibson in the Premier League this season.
And the three players could also share landmark moments in their own personal playing careers as we head to Stamford Bridge on Monday evening.
Leadbitter and Friend and Boro's longest-serving players, having joined from Ipswich Town and Doncaster Rovers respectively in the summer of 2012. The pair could make their 200th Boro appearances.
Meanwhile, Gibson - who has not missed a minute of league action this season - will celebrate a 200th career appearance in his next outing, having played his 150th Boro game against Manchester City last Sunday.